9
]zo}mrlojr kmmj}} vriulhjh o| ' Kmmj}} vklh o| xbj s ZMCK Clorkr| Dizr`kc ie Gjhlml`kc Mbjgl}xr| l} vzocl}bjh o| xbj Kgjrlmk` Mbjglmkc ]imljx|. ;;:: ]lxjj`xb ]xrjjx @.Q.# Qk}bl`axi`# HM ?66=5 Krxlmcj ]|`xbjxlm ]xzhlj} ie @jimcjrihk`j Hlxjrvj`j} erig ]kculk hlul`irzg 4¦ Vrjvkrkxli` k`h Ivlilh _jmjvxir Kmxlulx| ie ]kcul`lml` K`kciazj} Hj`l}j ]. ]lgv}i`# Vjxjr C. Nkxkulm# K`xbi`| Citkgk# Qk|`j Q. Bkrhl`a# Hkgi` Vkrrl}b# Djeerj| _. Hj}mbkgv}# Mbrl}xl`k G. Hjr}mb# Dib` ]. Vkrxlcck# _lmbkrh O. _ixbgk`# Bjr`k` @kukrri# k`h Xbigk} J. Vrl}l`tk`i D. Gjh. Mbjg.# ?661# :6 ";:,# =:<5'=56=HIL4 ;6.;6?;)dg616=<=h Vzoclmkxli` Hkxj "Qjo,4 ?6 Dz`j ?661 Hiq`cikhjh erig bxxv4))vzo}.km}.ira i` Ejorzkr| ;=# ?66< Girj Koizx Xbl} Krxlmcj Khhlxli`kc rj}izrmj} k`h ejkxzrj} k}}imlkxjh qlxb xbl} krxlmcj krj kuklckocj qlxbl` xbj BXGC ujr}li`4 ]zvvirxl`a L`eirgkxli` Cl`n} x i xbj = kr xlm cj} x bkx mlx j xbl} krxl mcj# k} ie x bj x lgj ie x bl} k rxl mcj h iq`cikh Kmmj }} xi blab rj} ic zxli` elazrj} Cl `n} x i krxlmcj} k`h mi`xj`x rjckx jh xi xbl} kr xl mc j Miv|rl abx vjr gl} }li` x i rjvr ihz mj e lazr j} k`h)ir xj x e rig xbl } krxl mcj

Denise S. Simpson et al- Synthetic Studies of Neoclerodane Diterpenes from Salvia divinorum: Preparation and Opioid Receptor Activity of Salvinicin Analogues

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8/3/2019 Denise S. Simpson et al- Synthetic Studies of Neoclerodane Diterpenes from Salvia divinorum: Preparation and Opi…

http://slidepdf.com/reader/full/denise-s-simpson-et-al-synthetic-studies-of-neoclerodane-diterpenes-from 1/9

]zo}mrlojr kmmj}} vriulhjh o| ' Kmmj}} vklh o| xbj s ZMCK Clorkr|

Dizr`kc ie Gjhlml`kc Mbjgl}xr| l} vzocl}bjh o| xbj Kgjrlmk` Mbjglmkc ]imljx|. ;;::]lxjj`xb ]xrjjx @.Q.# Qk}bl`axi`# HM ?66=5

Krxlmcj

]|`xbjxlm ]xzhlj} ie @jimcjrihk`j Hlxjrvj`j} erig ]kculk hlul`irzg 4¦Vrjvkrkxli` k`h Ivlilh _jmjvxir Kmxlulx| ie ]kcul`lml` K`kciazj}

Hj`l}j ]. ]lgv}i`# Vjxjr C. Nkxkulm# K`xbi`| Citkgk# Qk|`j Q. Bkrhl`a#Hkgi` Vkrrl}b# Djeerj| _. Hj}mbkgv}# Mbrl}xl`k G. Hjr}mb# Dib` ].

Vkrxlcck# _lmbkrh O. _ixbgk`# Bjr`k` @kukrri# k`h Xbigk} J. Vrl}l`tk`i

D. Gjh. Mbjg.# ?661# :6 ";:,# =:<5'=56=  HIL4 ;6.;6?;)dg616=<=h   Vzoclmkxli` Hkxj "Qjo,4 ?6 Dz`j ?661

Hiq`cikhjh erig bxxv4))vzo}.km}.ira i` Ejorzkr| ;=# ?66<

Girj Koizx Xbl} Krxlmcj

Khhlxli`kc rj}izrmj} k`h ejkxzrj} k}}imlkxjh qlxb xbl} krxlmcj krj kuklckocj qlxbl` xbj BXGC ujr}li`4

  ]zvvirxl`a L`eirgkxli`  Cl`n} xi xbj = krxlmcj} xbkx mlxj xbl} krxlmcj# k} ie xbj xlgj ie xbl} krxlmcj hiq cikh  Kmmj}} xi blab rj}iczxli` elazrj}

  Cl n} xi krxlmcj} k`h mi`xj`x rjckxjh xi xbl} krxlmcj  Miv|rlabx vjrgl}}li` xi rjvrihzmj elazrj} k`h)ir xjx erig xbl} krxlmcj

8/3/2019 Denise S. Simpson et al- Synthetic Studies of Neoclerodane Diterpenes from Salvia divinorum: Preparation and Opi…

http://slidepdf.com/reader/full/denise-s-simpson-et-al-synthetic-studies-of-neoclerodane-diterpenes-from 2/9

]|`xbjxlm ]xzhlj} ie @jimcjrihk`j Hlxjrvj`j} erig ]kc Qlk hlQl`irzg4 Vrjvkrkxli` k`h

Ivlilh _jmjvxir Kmxlulx| ie ]kcul`lml` K`kciazj}

Hj`l}j ]. ]lgv}i`#… Vjxjr C. Nkxkulm#… K`xbi`| Citkgk#… Qk|`j Q. Bkrhl`a#…#‡ Hkgi` Vkrrl}b#¡ Djeerj| _. Hj}mbkgv}#¡

Mbrl}xl`k G. Hjr}mb#ss Dib` ]. Vkrxlcck#ss _lmbkrh O. _ixbgk`#ss Bjr`k` @kukrri#⊪ k`h Xbigk} J. Vrl}l`tk`i$#…

 HlUl}li` ie Gjhlml`kc % @kxzrkc Vrihzmx} Mbjgl}xr|# Miccjaj ie Vbkrgkm|# Xbj Z`lUjr}lx| ie Liqk# Liqk Mlx|# Liqk :??8?# @kUkc _j}jkrmb

 Ckoirkxir|# 8::: IUjrciin KUj`zj# ]Q# Qk}bl`axi`# HM ?61=:# _j}jkrmb Xrlk`acj L`}xlxzxj# _j}jkrmb Xrlk`acj Vkrn# @irxb Mkricl`k ?116<#

k`h Mcl`lmkc V}|mbivbkrgkmicia| ]jmxli`# L_V# @LHK# @LB# HBB]# Okcxlgirj# Gkr|ck`h ?;??8

 _jmjlUjh Kvrlc =# ?661 

Ezrxbjr gihlelmkxli` ie }kcul`irl` K ";k,# xbj gkdir kmxluj migvi`j`x ie ]kcUlk hlUl`irzg# bk} rj}zcxjh l`xbj }|`xbj}l} ie `iujc `jimcjrihk`j hlxjrvj`j} qlxb ivlilh rjmjvxir keel`lx| k`h kmxlulx|. Qj rjvirx l` xbl}}xzh| xbkx ikhlkticj ;;k k`h }kculhlul` K ";?k,# k vbixii|aj`kxli` vrihzmx ie  ;k# bkuj ojj` lhj`xleljhk} xbj elr}x `jimcjrihk`j hlxjrvj`j} qlxb δ k`xkai`l}x kmxlulx|. Xbl} l`hlmkxj} xbkx khhlxli`kc }xrzmxzrkcgihlelmkxli`} ie ;k gk| cjkh xi k`kciazj} qlxb blabjr vixj`m| k`h zxlclx| k} hrza koz}j gjhlmkxli`}.

L`xrihzmxli`

]kcUlk hlUl`irzg "Jvcl`a % Dkxluk'G# Ckglkmjkj, bk} ojj`z}jh eir mj`xzrlj} l` mjrjgi`lkc rlxzkc} o| xbj Gktkxjm L`hlk`}

ie Ikkmk# Gjlmi.;

Xknj` l` ckraj hi}j} "?6'

56 vklr} ie erj}bcjkuj}, k` l`ez}li` ie  ]. hlUl`irzg l} rjvirxjh xi l`hzmj irkc#kzrkc# ir ul}li`kr| bkcczml`kxir| jvjrlj`mj}.? L` }zobkcczml`i'aj`lm hi}j} "eizr ir eluj erj}b cjkuj}, k` l`ez}li` l} z}jhgjhlml`kcc| xi mzrj k`jglk# bjkhkmbj# rbjzgkxl}g# k`h xbjhl}jk}j vk`ti` hj okrrjai "}qiccj` kohigj`,.? Mbjql`a erj}bcjkuj} ir }ginl`a hrljh cjkuj} qlcc kc}i vrihzmj bkcczml`iaj`lm'clnj jvjrlj`mj}.;#=': ]. hlUl`irzg cjkuj}# xl`mxzrj}# k`h jxrkmx}mk` oj rjkhlc| vzrmbk}jh i` xbj L`xjr`jx# k`h |iz`a khzcx} bkujojaz` xi jvjrlgj`x qlxb xbl} rjkhlc| kuklckocj# bkcczml`iaj`lm}zo}xk`mj.5'2 Mzrrj`xc|# xbj vck`x l} z`rjazckxjh l` xbj Z`lxjh]xkxj} ozx l} rjazckxjh l` k `zgojr ie Jzrivjk` miz`xrlj} k`hl` Kz}xrkclk. Iql`a xi lx} ariql`a vivzckrlx| k} k rjmrjkxli`kchrza# xbj HJK bk} rjmj`xc| vckmjh ]. hlUl`irzg i` xbj cl}x ie 

–hrza} ie mi`mjr`‗.Xbj l`xjrj}xl`a vbkrgkmicialmkc kmxlulx| ie ]. hlUl`irzg bk}cjh xi }jujrkc vb|ximbjglmkc l`uj}xlakxli`} ie xbj vck`x.<';:

Kgi`a xbj mi`}xlxzj`x} lhj`xleljh l} xbj `jimcjrihk`j hlxjrvj`j}kcul`irl` K ";k# Elazrj ;,.<';; ]kcul`irl` K ";k, vi}}j}}j}vixj`x bkcczml`iaj`lm kmxlulx|> k }ginjh hi}j ie ?66':66 ºavrihzmj} vrieiz`h bkcczml`kxli`} ck}xl`a zv xi k` bizr# xbz}rlukcl`a xbj vixj`m| ie xbj }|`xbjxlm bkcczml`iaj` C]H.8 ;k qk}eiz`h xi oj k vixj`x k`h }jcjmxluj δ'ivlilh rjmjvxir kai`l}x.;5

K `zgojr ie rjmj`x rjvirx} bkuj ezrxbjr himzgj`xjh xbj l` uluivbkrgkmicialmkc jeejmx} ie ;k.;1 Lx bk} ojj` }biq` xbkx ;k bk}hjvrj}}luj'clnj jeejmx} l` k eirmjh }qlg xj}x# hl}rzvx} mclgol`aojbkulir i` k` l`ujrxjh }mrjj` xk}n# k`h bk} rjqkrhl`a jeejmx}xbkx krj hleejrj`x erig lx} gixir kmxlulx|.;2'?6 Ixbjr rjvirx} bkuj

eimz}jh i` xbj k`xl`imlmjvxluj kmxlulx| ie ;k.?;'

?8 Xbj}j }xzhlj}rjujkcjh xbkx ;k vrihzmj} k hi}j'hjvj`hj`x k`xl`imlmjvxlujjeejmx xbkx qk} gjhlkxjh o| xbj δ ivlilh rjmjvxir "δI_, k`h l}}birx l` hzrkxli`. Xiajxbjr# xbj}j }xzhlj} mi`ejr k blab hjarjj

ie l`xjrj}x l` ;k k`h qj k`h ixbjr}# bkuj ojaz` xi ezrxbjr }xzh|lx} vbkrgkmicialmkc kmxli`}.

K} vkrx ie izr vriarkg xi }xzh| xbj vb|ximbjglmkc mi`}xlxz'j`x} ie ]. hlUl`irzg# qj rjmj`xc| lhj`xleljh xqi mi`aj`jr} ie ;k# }kcul`lml`} K "?k, k`h O "=k,.;8 Xbj}j migviz`h} qjrjl}ickxjh l` ciq |ljch erig k` kmjxi`j jxrkmx ie  ]. hlUl`irzg

k`h vi}}j}} k rkrj hlgjxbi|hlb|hri|xjxrkb|hriezrk` rl`a.]kcul`lml` K "?k, qk} eiz`h xi oj k vkrxlkc kai`l}x kx xbj δ

ivlilh rjmjvxir# qblcj }kcul`lml` O "=k, vi}}j}}jh º ivlilhk`xkai`l}x kmxlulx|.;8 Lx qk} l`xrlazl`a xi io}jruj erig xbj}jrj}zcx} xbkx xbj }xjrjimbjgl}xr| ie xbj hlgjxbi| arizv} ie xbjxjxrkb|hriezrk` rl`a qk} lgvirxk`x eir }jcjmxlulx| k`h kmxlulx|kgi`a xbj ivlilh rjmjvxir}. Xbj gicjmzckr ok}l} eir xbj}jhleejrj`mj} qk} `ix rjkhlc| mcjkr. Xbz}# qj }jx izx xi jvcirjxbj }xrzmxzrj'kmxlulx| rjckxli`}blv} ie  ?k k`h =k kx ivlilhrjmjvxir}. Bjrjl`# qj rjvirx xbj }jgl}|`xbj}l} k`h olicialmkckmxlulx| ie ezrk`'gihleljh k`kciazj} ie  ;k.

Mbjgl}xr|

Hlxjrvj`j ;k qk} jxrkmxjh erig miggjrmlkcc| kuklckocj hrljh]. hlUl`irzg cjkuj} k} hj}mrlojh vrjuliz}c|.?: Xbj xrjkxgj`xie  ;k qlxb @ 'origi}zmml lglhj l` kmjxi`lxrlcj keeirhjh ori'giezrk` 8.?5 Kcxjr`kxlujc|# xbj rjkmxli` ie ;k qlxb Or? l` GjIBkx ciq xjgvjrkxzrj keeirhjh xbj hlgjxbi| kcnj`j hjrlukxluj":, k} k glxzrj ie ml} k`h xrk`} l}igjr} "]mbjgj ;,.?5 _jhzmxli`ie : qlxb rbihlzg i` mkroi` keeirhjh xrk`} hlgjxbi|xjxrkb|'hriezrk` l}igjr} 5.?1 B|hriaj`kxli` ie  ;k z}l`a rbihlzg i`mkroi` keeirhjh k ;4; glxzrj ie  1 k`h kmlh 2.?2 Ezrxbjrvzrlelmkxli` ie ";= _,'1 z}l`a BVCM akuj k glxzrj ie k gkdirvjkn k`h }jujrkc gl`ir migvi`j`x} xbkx qjrj `ix ioxkl`jh l`}zeelmlj`x {zk`xlxlj} eir lhj`xlelmkxli`. K`kc|}l} ie xbj ;B @G_#;=M @G_# BGOM# k`h BG[M hkxk ie ";= _,'1 cjh xi xbjk}}la`gj`x ie xbj ari}} }xrzmxzrj. Xbj rjckxluj }xjrjimbjgl}xr|kx M;= qk} hjrlujh erig xbj @IJ]\ hkxk. Xbj @IJ]\}vjmxrzg ie xbj gkdir vjkn ie ";= _,'1 }biqjh mri}}'vjkn}ojxqjj` B;?# B;=# k`h MB='?6. Xbj}j mirrjckxli`} }zaaj}xjhxbkx xbj}j vrixi`} qjrj mci}j l` }vkmj. Xbj ko}iczxj }xjrji'mbjgl}xr| kx M;= qk} hjxjrgl`jh xi oj _ erig xbj }l`acj'mr|}xkcR'rk| hkxk "Elazrj ?,.

Xbj xrjkxgj`x ie  ;k qlxb @kLI8 k`h k mkxkc|xlm kgiz`x ie _zMc= keeirhjh xbj mirrj}vi`hl`a M;= kmlh.?1 Xbj mizvcl`a ie xbj M;= kmlh qlxb }jcj`ivbj`ic eicciqjh o| hjmkroi`|ckxli`qlxb Oz=]`B k`h KLO@ keeirhjh < "]mbjgj ?,.?1 Khhlxli`kc

$ Mirrj}vi`hl`a kzxbir. Xjcjvbi j4 "=;<, ==:'5<?6. Ek4 "=;<, ==:'2155. J'gklc4 xbigk}'vrl}l`tk`iFzliqk.jhz.

… Xbj Z`lujr}lx| ie Liqk.‡ Vrj}j`x Khhrj}}4 Hjvkrxgj`x ie Mbjgl}xr|# Bz xjr Miccjaj ie MZ@\#

@jq \irn# @jq \irn ;66?;.¡ @kukc _j}jkrmb Ckoirkxir|.ss @LB.⊪ _j}jkrmb Xrlk`acj L`}xlxzxj.

=:<5 D. Gjh. Mbjg. ?661# :6# =:<5'=56=

;6.;6?;)dg616=<=h MMM4 (=1.66 ¬ ?661 Kgjrlmk` Mbjglmkc ]imljx|Vzocl}bjh i` Qjo 65)?6)?661

8/3/2019 Denise S. Simpson et al- Synthetic Studies of Neoclerodane Diterpenes from Salvia divinorum: Preparation and Opi…

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mizvcl`a ie xbj M;= kmlh qlxb jlxbjr kgl`ijxbk`ic ir kmjxkglhjilgj z}l`a JHML eicciqjh o| m|mcltkxli` keeirhjh ;6 k`h kglxzrj ie ;;k k`h ;;o# rj}vjmxlujc|. Vbixiilhkxli` ie  ;k l`xbj vrj}j`mj ie }z`clabx keeirhjh ν'b|hri|ozxj`iclhj} ;?k k`h;?o.?< Qblcj izr }xzhlj} qjrj l` vriarj}}# }kculhlul` K ";?k,k`h }kculhlul` O ";?o, qjrj rjvirxjh erig k gjxbk`ic jxrkmx

ie miggjrmlkcc| kuklckocj hrljh ]. hlUl`irzg cjkuj}.=6

Xbl}}|`xbj}l} l} xbjrjeirj xbj elr}x rjvirxjh vrjvkrkxli` ie }kculhlul`}K k`h O erig ;k.

Aluj` xbj }zmmj}} ie xbj vzrlelmkxli` ie  1 z}l`a BVCM# qj}izabx xi }jvkrkxj xbj gkdir }xjrjil}igjr} ie  : "]mbjgj =,.Xbj glxzrj ie ml} k`h xrk`} l}igjr} ie : qk} vzrleljh o| BVCMxi aluj migviz`h} ;=k k`h ;=o. Xbj ari}} }xrzmxzrj} ie  ;=k

k`h ;=o qjrj k}}la`jh ok}jh i` ;B @G_# ;=M @G_# BGOM#MI]\# k`h BG[M hkxk "Xkocj ;,. Eir ;=o# xbj @IJ]\}vjmxrzg }biqjh mri}}'vjkn} ojxqjj` B;: k`h B;5# B;: k`hB;?# k`h B;5 k`h B;?. Xbl} l`hlmkxjh xbkx B;: k`h B;5 qjrji` xbj }kgj ekmj ie xbj gicjmzcj k} B;?. B;: k`h B;5 qjrjxbjrjeirj k}}la jh k} _ rjckxluj xi B;?. Eir ;=k# xbj rjckxluj}xjrjimbjgl}xr| ie M;8 xi M;5 qk} k}}la`jh o| mkrjezc k`kc|}l}

ie xbj @IJ]\ hkxk k`h o| migvkrl}i` xi xbj @IJ]\ }vjmxrzgie  ;=o. L` xbj @IJ]\ }vjmxrzg ie  ;=k# `i mri}}'vjkn} qjrj}jj` ojxqjj` B;: k`h B;5. Mri}}'vjkn} qjrj julhj`x ojxqjj`B;? k`h B;:. Qblcj xbj ko}j`mj ie @IJ“} ojxqjj` B;: k`hB;5 l} ix mi`mcz}luj julhj`mj eir }xjrjimbjglmkc k}}la`gj`x}#xbj vrj}j`mj ie @IJ“} ojxqjj` B;: k`h B;5 ie  ;=o# k} qjcck} xbj vrj}j`mj ie B;?)B;: @IJ“} l` ;=k# cjh z} xi vrivi}jxbj xrk`}'hlgjxbi| }xrzmxzrj ie ;=k.

El`kcc|# xbj ;:#;5'hlgjxbi|xjxrkb|hriezrk` l}igjr} 5 qjrj}jvkrkxjh o| BVCM xi |ljch k} xbj gkdir vrihzmx} xbj xrk`}';:#;5'hlgjxbi|xjxrkb|hriezrk`} ;8k k`h ;8o "]mbjgj 8,. Xbj}xrzmxzrj} ie  ;8k k`h ;8o qjrj k}}la`jh i` xbj ok}l} ie  ;B@G_# ;=M @G_# BGOM# MI]\# k`h BG[M hkxk "Xkocj ?,.Eir ;8k# @IJ]\ mirrjckxli`} qjrj io}jrujh ojxqjj` B;?# B;=#k`h B;:. @i mri}}'vjkn} qjrj }jj` ojxqjj` B;: k`h B;5.Mri}}'vjkn} qjrj julhj`x ojxqjj` xbj MB=I';: k`h B;5 k`hojxqjj` MB=I';5 k`h B;:. Xbz}# o| k`kcia| xi xbj ;= }jrlj}ie k`kciazj}# xbj rjckxluj }xjrjimbjgl}xr| k} }biq` eir ;8k l}vrivi}jh. Eir ;8o# xbjrj qjrj `i @IJ mirrjckxli`} ojxqjj`

B;: k`h B;5. Mri}}'vjkn} qjrj io}jrujh ojxqjj` B;?# B;5#B;=# k`h MB='?6# k`h B;6# MB=I';:# k`h B;:. Xbj}j hkxkl`hlmkxjh xbkx xbj rjckxluj }xjrjimbjgl}xr| ie ;8o l} k} }biq`.

Olicialmkc _j}zcx}

Migviz`h} ;o k`h ?';8 qjrj xbj` jukczkxjh eir keel`lx| kxbzgk` ivlilh rjmjvxir} z}l`a gjxbihicia| vrjuliz}c| hj}mrlojh"Xkocj =,.=; L` k` jkrcljr }xzh|# ;k qk} eiz`h xi bkuj blabkeel`lx| "N l , ;.< `G, k`h }jcjmxlulx| eir δ rjmjvxir} iujr θrjmjvxir}.?; ]kcul`irl` O ";o, qk} eiz`h xi bkuj ;81'eich ciqjrkeel`lx| kx δI_} migvkrjh xi ;k "N l , ?26 `G u} N l ,

;.< `G, k`h `jaclalocj keel`lx| kx º k`h θ rjmjvxir} "N l 0

;6 666 `G,. Xi ekmlclxkxj hlrjmx migvkrl}i` qlxb ;k# }kcul`lml`}K "?k, k`h O "=k, qjrj rjjukczkxjh eir ivlilh rjmjvxir keel`lx|.

Elazrj ;. ]xrzmxzrj} ie }kcul`irl` K ";k,# }kcul`irl` O ";o,# }kcul`lml` K "?k,# k`h }kcul`lml` O "=k,.

]mbjgj ;k

k _jkaj`x} k`h mi`hlxli`}4 "k, @O]# MB=M@> "o, Or?# GjIB# MB?Mc?#'=6 ¶M> "m, B?# _b)M# GjIB> "h, B?# _b)M# MB?Mc?  )GjIB> "j, BVCM"86* MB=M@)56* B?I,.

Elazrj ?. R'rk| mr|}xkcciarkvblm }xrzmxzrj ie ";= _,'1.

 @jimcjrihk`j Hlxjrvj`j} erig ]kcUlk hlUl`irzg Dizr`kc ie Gjhlml`kc Mbjgl}xr|# ?661# Uic. :6# @i. ;: =:<1

8/3/2019 Denise S. Simpson et al- Synthetic Studies of Neoclerodane Diterpenes from Salvia divinorum: Preparation and Opi…

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Hlxjrvj`j} ?k k`h =k qjrj eiz`h xi bkuj arjkxc| rjhzmjh keel`lx|eir δI_} migvkrjh xi ;k "N l , =<6 `G k`h N l , 16?6 `G u}N l , ;.< `G, k`h `jaclalocj keel`lx| eir º ir θ rjmjvxir} "N l 0

;6 666 `G,. Izr jeeirx} xbj` }blexjh xi ezrxbjr vrioj xbj jeejmx}ie xbj ezrk` rl`a ie  ;k'=k.

]jcjmxluj kmjx|ckxli` ie xbj M;8 b|hri|c arizv ie  ?k k`h=k keeirhjh ?o k`h =o# rj}vjmxlujc|. M;8 kmjx|ckxli` qk} `ixxicjrkxjh# k} }la`lelmk`x keel`lx| kx º# θ# k`h δ rjmjvxir} qk}

ci}x "N l 0 ;6 666 `G,. Biqjujr# origl`kxli` ie xbj ezrk` rl`aie ;k qk} qjcc'xicjrkxjh# k} migviz`h 8 rjxkl`jh blab keel`lx|eir δI_} "N l , =.6 `G u} N l , ;.< `G, k`h }jcjmxlulx| iujr ºk`h θ rjmjvxir} " º ) δ , 82= k`h θ ) δ , ?:86# rj}vjmxlujc|,._jgiukc ie xbj M;= k`h M;8 b|hri|c arizv} k`h l`xrihzmxli`ie k` kcnj`j ojxqjj` M;= k`h M;8 ie  ?k k`h =k keeirh}hlgjxbi|hlb|hriezrk` :. L`lxlkcc|# : qk} jukczkxjh k} k glxzrjie }xjrjil}igjr}# ok}jh i` xbj jk}j ie }|`xbj}l}.?5 Kcnj`j :

qk} eiz`h xi bkuj `jaclalocj keel`lx| eir º k`h θ rjmjvxir} "N l0;6 666 `G, ozx xi bkuj }lglckr keel`lx| kx δI_} migvkrjh xi?k "N l , 886 `G u} N l , =<6 `G,. Xbl} l`hlmkxjh xbkx xbj M;=k`h M;8 b|hri|c arizv} l` ?k k`h =k krj `ix rj{zlrjh eir blabkeel`lx| ol`hl`a. Xi ezrxbjr vrioj xbl} el`hl`a# xbj M;= kcnj`jl` : qk} rjhzmjh xi keeirh 5.?1 L`xjrj}xl`ac|# xbl} gihlelmkxli`

rj}zcxjh l` k` ;;'eich l`mrjk}j l` keel`lx| kx δI_} "N l ,

886 `G u} N l , 86 `G,. Xi izr }zrvrl}j# xbl} gihlelmkxli`kc}i l`mrjk}jh keel`lx| kvvrilgkxjc| ?'eich kx ºI_} "N l ,

82;6 `G u} N l 0 ;6 666 `G,._jgiukc ie xbj gjxbi| arizv} l` 5 keeirh} xjxrkb|hriezrk`

1.?2 Xbl} mbk`aj rj}zcxjh l` k` kvvrilgkxjc| ='eich l`mrjk}jl` keel`lx| kx δI_} migvkrjh xi 5 "N l , ;8 `G u} N l ,

86 `G,. K vrjuliz} rjvirx }biqjh xbkx 1 bkh =<'eich cj}}

keel`lx| eir δI_} migvkrjh xi ;k.?2

L` izr bk`h}# 1 bkh 1'eichciqjr keel`lx| eir δI_} migvkrjh xi ;k "N l , ;8 `G u} N l ,

;.< `G,. I`j rjk}i` eir xbl} hl}mrjvk`m| mizch oj xbj z}j ie ^;?:LWLIR\ rkxbjr xbk` ^=BWZ5<#:<= z}jh o| xbj ixbjr rj}jkrmbarizv k} xbj rkhliclak`h. L` }|`xbj}ltl`a 1# k gkdir }lhj vrihzmxl} kmlh 2. Xbl} migviz`h kc}i aluj} }igj l`}labx k} xi qbjxbjrxbj l`xkmx ckmxi`j rl`a l} `jjhjh eir blab keel`lx| ol`hl`a kxδI_}. Hlxjrvj`j 2 bkh 5:'eich cj}} keel`lx| eir δI_} migvkrjhxi 1 "N l , <;6 `G u} N l , ;8 `G,# }zaaj}xl`a xbkx xbj ckmxi`jrl`a l} `jmj}}kr| eir blab keel`lx| ol`hl`a kx δI_}. Hlxjrvj`j";= _,'1 rjxkl`jh blab keel`lx| eir δI_} migvkrjh xi ;k "N l ,

=.1 `G u} N l , ;.< `G,. Xbl} rj}zcx l`hlmkxj} xbkx k` krigkxlmrl`a l} `ix `jmj}}kr| eir blab keel`lx| kx δI_}. Biqjujr#migvcjxj rjgiukc ie xbj ezrk` rl`a "<,?1 rj}zcxjh l` iujr k ;166'

]mbjgj ?k

k _jkaj x} k`h mi`hlxli }4 "k, _zMc=±=B?I# @kLI8# MMc8 )MB=M@)B?I> "o, VbIVIMc?# M5B:]jB# @Jx=# XBE> "m, Oz=]`B# KLO@# xiczj`j> "h, JHML#BIOx# jxbk`ickgl`j# @Jx=# MB?Mc?> "j, Hjii'Eczir# MB?Mc?# '=6 ¶M> "a, JHML# MB=M"@B?,h@IB# MB?Mc?> "a, xiczj`j# bjkx> "b, vbixilhkxli` l` xbjvrj}j`mj ie }z`clabx.

]mbjgj =k

k _jkaj x} k`h mi`hlxli }4 "k, BVCM ^86* MB=M@)56* B?I "6.;* XEK,W.

=:<2 Dizr`kc ie Gjhlml`kc Mbjgl}xr|# ?661# Uic. :6# @i. ;: ]lgv}i` jx kc.

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eich ci}} l` keel`lx| kx δI_} migvkrjh xi ;k "N l , =866 `G u}N l , ;.< `G,. _jvckmjgj`x ie xbj ='}zo}xlxzxjh ezrk` rl`a qlxbk ?'ikticl`j rl`a ";6, rj}zcxjh l` iujr k ;:6'eich ci}} l` keel`lx|"N l , =66 `G u} N l , ;.< `G,. ]zo}xlxzxli` ie xbj ezrk` rl`aqlxb k 8'gjxb|c';#=#:'ikhlkticl`j rl`a ";;k, rj}zcxjh l` k ?<'eich ci}} l` keel`lx| migvkrjh xi ;k "N l ,

:5 `G u} N l , ;.< `G,. L`ujr}li` ie xbj M2 }xjrjimbjgl}xr|ie  ;;k ";;o, rjhzmjh keel`lx| ;2'eich eir δI_} migvkrjh xi;;k "N l , <<6 `G u} N l , :5 `G,.

Mbrigkxiarkvblm }jvkrkxli` ie : keeirh} ;=k k`h ;=o. Xrk`}'

l}igjr ;=k bkh }lglckr keel`lx| eirδ

I_} migvkrjh xi : "N l,

8?6 `G u} N l , 886 `G,. Biqjujr# ;=k bkh kvvrilgkxjc|='eich blabjr keel`lx| eir ºI_} xbk` : "N l , =;<6 `G u} N l0;6 666 `G,. L`ujr}li` ie xbj M;5 }xjrjimbjgl}xr| ie ;=k ";=o,l`mrjk}jh keel`lx| ?'eich eir δI_} "N l , ;26 `G u} N l ,

886 `G, ozx bkh clxxcj jeejmx i` keel`lx| eir ºI_} "N l ,

=186 `G u} N l , =;<6 `G,. Xbj xrk`}'?#:'hlgjxbi| k`kciazj}ie ";= _,'1# ;8k k`h ;8o# }biqjh blab keel`lx| eir δI_} ";8k#N l , ?: `G k`h ;8o# N l , ;?: `G,. Biqjujr# ;8k bkh 1'eichciqjr keel`lx| eir δI_} migvkrjh xi ";= _,'1 "N l , ?: `G u}N l , =.1 `G,.

Xi ezrxbjr jvcirj xbj}j hjujcivgj`x}# 8# ";= _,'1# ;;k# ;?k#;=k# ;=o# ;8k# k`h ;8o qjrj jukczkxjh eir kmxlulx| kx ivlilhrjmjvxir} z}l`a xbj ^=:]WAXV'ν'] ol`hl`a k}}k| "Xkocj 8,.?;#?5

Origi k`kciazj 8 qk} eiz`h xi oj k ezcc kai`l}x kx δI_}" J gk , ;68* rjckxluj xi xbj ezcc kai`l}x Z5<#:<=, j{zlvixj`xqlxb ;k "JM:6 , :6 `G u} JM:6 , 8: `G,. Xbl} }zaaj}x} xbkx8# le ckojcjh qlxb 15Or# glabx bkuj vixj`xlkc zxlclx| k} k δI_}jcjmxluj VJX lgkal`a kaj`x. Xjxrkb|hriezrk` ";= _,'1 qk} ;1'eich cj}} vixj`x kx δI_} xbk` ;k "JM:6 , 1:6 `G u} JM:6 ,

8: `G, k`h l} k vkrxlkc kai`l}x " J gk , 18* rjckxluj xi Z5<#':<=,. Xbl} l} l` mi`xrk}x xi vrjuliz} el`hl`a} xbkx }biqjh xbkx1 qk} ='eich cj}} kmxluj xbk` ;k "JM:6 , ;?5 `G u} JM:6 ,

85 `G,.?2 I`j vixj`xlkc rjk}i` eir xbl} hl}mrjvk`m| l} xbkx xbj

eirgjrc| jukczkxjh xjxrkb|hriezrk` k`kciazj qk} xj}xjh k} kglxzrj ie M;= jvlgjr}. Izr rj}zcx} erig jukczkxli` ie xbj ;= _

jvlgjr lgvc| xbkx xbj ;=] jvlgjr gk| bkuj blabjr kmxlulx|.Xbl}# biqjujr# `jjh} ukclhkxli` xbrizab }|`xbj}l} k`h xj}xl`a.

Aluj` xbj kmxlulx| }jj` qlxb ";= _,'1# qj xbj` jukczkxjh ;;k#;;o# k`h ;?k eir kmxlulx| kx ivlilh rjmjvxir}. Ikhlkticj ;;k

qk} eiz`h xi bkuj k`xkai`l}x kmxlulx| kx ºI_} "N j , 8=6 `G,k`h δI_} "N j , =56 `G,. Xbl} l} xbj elr}x rjvirx ie k`jimcjrihk`j hlxjrvj`j qlxb δ k`xkai`l}x kmxlulx| k`h lhj`xlelj}lx k} k `iujc }mkeeich eir δI_ k`xkai`l}x}. Xbj M2 jvlgjr ie ;;k ";;o, bkh 8'eich ciqjr kmxlulx| kx ºI_} "N j , ;:=6 u} N j, 8=6 `G, k`h ;5'eich ciqjr kmxlulx| kx δI_} "N j , :526 k`hN j , =56 `G, migvkrjh xi ;;k. ]kculhlul` K ";?k,# kvbixiilhkxli` vrihzmx ie ;k# bkh }lglckr k`xkai`l}x kmxlulx| kx

Xkocj ;. @G_ ]vjmxri}mivlm Hkxk "566 GBt# MHMc=, eir ;=k k`h ;=o

;=k ;=o

vi}lxli` θM# gzcx θB# gzcx " D l` Bt, θM# gzcx θB# gzcx " D l` Bt,

; ?6?.;?# M ?6?.;1# M? 1:.6;# MB :.;5# g 18.<2# MB :.;2# g= =6.1<# MB? ?.=6# g =6.26# MB? ?.=?# g8 :=.56# MB ?.1?# hh "8.1# ;?.;, :=.56# MB ?.1=#hh "8.5# ;?.;,: 8?.62# M 8?.61# M5 =2.;?# MB? ;.::# g =2.;=# MB? ;.:5# g

;.26# hh "=.;# ;;.2, ;.26# hh "=.;# ;;.2,

1 ;2.;:# MB? ;.5?# g ;2.;=# MB? ;.5?# g?.;?# g ?.;?# g

2 :;.?2# MB ?.6?# hh "=.?# ;;.2, :;.=?# MB ?.6?# hh "=.?# ;;.2,< =:.?2# M =:.=;# M;6 58.;?# MB ?.;:# } 58.61# MB ?.;2# };; 86.85# MB? ;.::# g 86.12# MB? ;.::# g

?.81# hh ":.:# ;=.8, ?.:6# hh ":.8# ;=.8,;? 1;.58# MB :.;8# g 1?.6;# MB :.;5# g;= ;8=.21# M ;8=.2;# M;8 ;?1.?5# MB :.<;# h ";.?, ;?5.::# MB :.<?# h ";.6,;: ;61.?5# MB :.22# h "=.2, ;65.:5# MB :.56# h "5.;,;5 ;61.<1# MB :.2:# h ";.?, ;65.?5# MB :.<?# h# ";.6,;1 ;16.:1# M ;16.5<# M;2 ;1;.:8# M ;1;.::# M;< ;5.=1# MB= ;.;6# } ;5.=2# MB= ;.;?# }?6 ;:.=?# MB= ;.86# } ;:.?2# MB= ;.86# }IM IMB= "?, ;5<.<?# M ;5<.22# M

IMIMB = "8, ?6.56# MB= ?.;2# } ?6.56# MB= ?.?6# }MIIMB = "8, :?.66# MB= =.1?# } :?.66# MB= =.1:# }IMB = ";:, ::.;8# MB= =.8:# } ::.=;# MB= =.8:# }IMB = ";5, :8.=1# MB= =.=2# } :8.=<# MB= =.86# }

]mbjgj 8k

k _jkaj x} k`h mi`hlxli }4 "k, BVCM "=:* MB=M@)5:* B?I,.

 @jimcjrihk j Hlxjrvj j} erig ]kcUlk hlUl`irzg Dizr`kc ie Gjhlml`kc Mbjgl}xr|# ?661# Uic. :6# @i. ;: =:<<

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 ºI_} "N j , 156 u} N j , 8=6 `G, k`h δI_} "N j , 886 `Gk`h N j , =56 `G, migvkrjh xi ;;k.Hlb|hriezrk`} ;=k k`h ;=o qjrj xbj` jukczkxjh eir ez`mxli`kc

l`blolxli` ie ivlilh rjmjvxir}. Migviz`h} ;=k k`h ;=o qjrjeiz`h xi oj qjkn `i`}jcjmxluj k`xkai`l}x} kx º# θ# k`h δ

rjmjvxir}. Biqjujr# ;=o bkh ='eich blabjr kmxlulx| kx θ rjmjvxir}"N j , ;?26 `G u} N j , =?26 `G, k`h ?'eich blabjr kmxlulx|kx δ rjmjvxir} xbk` xbj xrk`} l}igjr ;=k "N j , ?=16 `G u} N j, <166 `G,. Xbl} l`hlmkxj} xbkx xbj ] mi`elazrkxli` ie xbj M;5gjxbi| arizv l} ekuirjh eir k`xkai`l}x kmxlulx|.

El`kcc|# xrk`}'hlgjxbi|xjxrkb|hriezrk`} ;8k k`h ;8o qjrjjukczkxjh l` xbj ez`mxli`kc k}}k|}. _jhzmxli` ie xbj kcnj`j l`;=k ";8k, l`mrjk}j} k`xkai`l}x vixj`m| kx ºI_} ?'eich "N j ,

;=16 `G u} N j , ?=?6 `G, k`h hjmrjk}j} vixj`m| kv'

vrilgkxjc| ='eich kx θI_} "N j 0;6 666 `G u} N j ,=?26 `G,. L`xjrj}xl`ac|# xbl} gihlelmkxli` kc}i mbk`ajh xbjkmxlulx| ie ;8k kx δI_} erig k` k`xkai`l}x l`xi k ezcc kai`l}x"JM:6 , ?=:6 `G# J gk , <:* rjckxluj xi Z5<#:<=,. Ezrxbjr'girj# ;8k l} ='eich cj}} vixj`x xbk` 1 kx δI_} "JM:6 ,

?=:6 `G u} JM:6 , 1:6 `G, ozx lx kvvjkrjh xi oj girjjeelmkmliz} " J gk , <:* u} J gk , 2;* rjckxluj xi Z5<#:<=,.Xbj}j hkxk l`hlmkxj xbkx xbj khhlxli` ie xbj gjxbi| arizv}hjmrjk}j} k`xkai`l}x kmxlulx| kx º k`h θI_} ozx lgvkrx} k`kai`l}x mi`eirgkxli kx δ rjmjvxir}. Ck}x# ;8o qk} eiz`h xibkuj `i kmxlulx| "kai`l}x ir k`xkai`l}x, kx ivlilh rjmjvxir}.Miccjmxlujc|# xbj}j el`hl`a} l`hlmkxj xbkx khhlxli`kc }xrzmxzrkcgihlelmkxli`} xi xbj ezrk` rl`a ie  ;k gk| cjkh xi k`xkai`l}x}qlxb blabjr vixj`m|. Ezrxbjrgirj# xbj blabc| clvivblclm `kxzrj

Xkocj ?. @G_ ]vjmxri}mivlm Hkxk "566 GBt# MHMc=, eir ;8k k`h ;8o

;8k ;8o

vi}lxli` θM θB# gzcx " D l` Bt, θM θB# gzcx " D l` Bt,

; ?6?.6?# M ?6?.?;# M? 1:.6?# MB :.;:# g 18.<5# MB :.;:# g= =6.2;# MB? ?.=6# g =6.25# MB? ?.?2# g8 :=.:<# MB ?.18# hh ":.;# ;;.:, :=.56# MB ?.18# g: 8?.;;# M 8?.;?# M5 =2.;1# MB? ;.::# g =2.;<# MB? ;.12# h ";=.?,

;.12# hh "=.6# ;;.2, ;.::# g

1 ;2.;1# MB? ;.:2# g ;2.;<# MB? ;.5?# g?.;;# g ?.;;# g

2 :;.=5# MB ;.<=# g :;.==# MB ;.<=# hh "=.8# ;;.2,< =:.;;# M =:.;:# M;6 58.6<# MB ?.;?# } 58.?8# MB ?.;6# };; 8;.:?# MB? ;.?:# x ";?.1, 8;.?1# MB? ;.;?# x ";?.8,

?.=?# g ?.=<# hh ":.=# ;=.?,;? 15.:<# MB 8.:5# g 15.<:# MB 8.::# g;= :6.:=# MB ?.;2# g :6.<2# MB ?.;2# g;8 =?.:<# MB? ?.=6# g =?.;1# MB? ?.?=# g

;.<8# g ;.:1# g;: ;6:.=?# MB 8.<6# h "=.5, ;6:.6?# MB :.6:# hh# ";.<# :.=,;5 ;68.<<# MB :.;6# g ;65.=8# MB :.?=# h "6.2,;1 ;1;.61# M ;1;.6;# M;2 ;1;.:1# M ;1;.:2# M;< ;5.=?# MB= ;.6<# } ;5.=;# MB= ;.;6# }?6 ;:.;;# MB= ;.=:# } ;:.;1# MB= ;.=1# }

IM IMB= "?, ;5<.22# M ;5<.<?# MIMIMB = "8, ?6.5;# MB= ?.;1# } ?6.52# MB= ?.;2# }MIIMB = "8, :;.<2# MB= =.18# } :;.<1# MB= =.1?# }IMB = ";:, :5.61# MB= =.86# } ::.8<# MB= =.=2# }IMB = ";5, ::.51# MB= =.=2# } ::.62# MB= =.=?# }

Xkocj =. Ol`hl`a Keel`lxlj} ie ]kcul`irl` K K`kciazj} kx Ivlilh _jmjvxir} Z}l`a ^;?:LWLIR\ k} _khliclak`h=='=:

N l " ]H# `G }jcjmxlulx|

migvh º θ δ º ) δ θ ) δ

;kk 0;666o :1<6 " <26 ;.< " 6.? 0:?5 =6:6;o 0;6 666 0;6 666 ?26 " ?6 0=: 0=:?k 0;6 666 0;6 666 =<6 " =6 0?5 0?5?o 0;6 666 0;6 666 0;6 666 @Hm @H=k 0;6 666 0;6 666 16?6 " 1:6 ;.8 ;.8=o 0;6 666 0;6 666 0;6#666 @H @H

8 ;8:6 " 56 15?6 " ;26 =.6 " 6.? 82= ?:86: 0;6 666 0;6 666 886 " =6 0?6 0?65 82;6 " 8?6 0;6 666 86 " ; ;?6 0?:61 1?86 " 826 0;6 666 ;8 " ; :;1 1;8";= _,'1 <1<6 " ;6<6 0;6 666 =.1 " 6.? ?585 0?1662 0;6 666 0;6 666 <;6 " 86 0;6 0;6< 0;6 666 0;6 666 =866 " ;:6 0= 0=;6 0;6 666 0;6 666 =66 " ?6 0=6 0=6;;k 0;6 666 0;6 666 :5 " = 0;16 0;16;;o 0;6 666 0;6 666 <<6 " 56 0;6 0;6;=k =;<6 " ?=6 0;6 666 8?6 " ?6 2 0?=;=o =186 " ?86 0;6 666 ;26 " ?6 ?; 0::;8k 0;6 666 0;6 666 ?: " ; 0866 0866;8o 0;6 666 0;6 666 ;?: " 8 026 026

k Hkxk erig rje ?;. o Vkrxlkc l`blolxir. m @ix hjxjrgl`jh

=566 Dizr`kc ie Gjhlml`kc Mbjgl}xr|# ?661# Uic. :6# @i. ;: ]lgv}i` jx kc.

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ie  ?k k`h lx} k`kciazj} rkl}j} xbj vi}}lolclx| xbkx l`xjrkmxli`}qlxb xbj mjcc gjgork`j gk| l`eczj`mj xbj ol`hl`a ie xbj}jmigviz`h} xi xbj ivlilh rjmjvxir}.=?

Mi`mcz}li`

L` }zggkr|# qj bkuj jukczkxjh }jujrkc ezrk` rl`a gihleljhk`kciazj} ie  ;k eir ivlilh rjmjvxir keel`lx| k`h kmxlulx|. Xbl}vkvjr rjvirx} xbj elr}x }|`xbjxlm vrjvkrkxli` ie }kculhlul`} K";?k, k`h O ";?o,. Origi k`kciazj 8 bk} ojj` lhj`xleljh k} kvixj`x δI_ kai`l}x# k`h ikhlkticj ;;k k`h }kculhlul` K ";?k,bkuj ojj` lhj`xleljh k} xbj elr}x `jimcjrihk`j hlxjrvj`j} qlxb δ

k`xkai`l}x kmxlulx|. Kgi`a xbj }kcul`lml` k`kciazj}# lx kvvjkr}xbkx xbj ] mi`elazrkxli` ie xbj M;5 gjxbi| arizv l} ekuirjheir k`xkai`l}x kmxlulx|. ]|`xbjxlm rizxj} xi khhlxli`kc k`kciazj}ie ;k krj mzrrj`xc| ojl`a jvcirjh k`h qlcc oj rjvirxjh l` hzjmizr}j.

Jvjrlgj`xkc ]jmxli`

Z`cj}} ixbjrql}j l`hlmkxjh# kcc rjkaj`x} qjrj vzrmbk}jh erigmiggjrmlkc }zvvcljr} k`h qjrj z}jh qlxbizx ezrxbjr vzrlelmkxli`.Xbj ;B k`h ;=M @G_ }vjmxrk qjrj rjmirhjh kx =66 GBt i` kOrznjr Kuk`mj'=66 }vjmxrigjxjr ir i` k Orznjr KGR'566}vjmxrigjxjr z}l`a MHMc= k} }icuj`x# θ ukczj} l` vvg "XG] k}l`xjr`kc }xk`hkrh,# k`h D "Bt, k}}la`gj`x} ie ;B rj}i`k`mj mizvcl`a.BGOM k`h BG[M hkxk qjrj miccjmxjh i` xbj KGR'566 }vjm'xrigjxjr. Xbl`'ck|jr mbrigkxiarkvb| "XCM, qk} vjreirgjh i`6.?: gg K`kcxjmb ABCE }lclmk ajc vckxj}. ]vix} i` XCM qjrjul}zkcltjh qlxb uk`lccl`)B?]I8 l` JxIB. ]lclmk ajc "=?'5= ºgvkrxlmcj }ltj, erig Oihgk` L`hz}xrlj} "Kxck`xk# AK, qk} z}jh eirmiczg` mbrigkxiarkvb|. BVCM qk} mkrrljh izx i` k` Kalcj`x ;;66]jrlj} mkvlcckr| BVCM }|}xjg qlxb hlihj krrk| hjxjmxir. Vjkn} qjrjhjxjmxjh kx ?6<# ?;8# k`h ?:8 `g. GVCM qk} vjreirgjh i` k _X]mlj`xlelm VzrMbrig ;:6'AM] }|}xjg j{zlvvjh qlxb k }lclmk ajcmiczg` ";.; mg Ñ =6 mg,. Xbj vzrlx| ie xbj migviz`h} qk}

hjxjrgl`jh i` k` k`kc|xlmkc }mkcj o| BVCM i` xbj }kgj l`}xrzgj`xhj}mrlojh koiuj. K` Kalcj`x Jmclv}j RHO'M;2 miczg` "8.5 ggÑ ;:6 gg# : ºg, qk} zxlcltjh eir xbj}j k`kc|}j}.

Vzrlelmkxli` ie ";= _,'1. Xbj mrzhj vrihzmx erig xbj _b)Mb|hriaj`kxli` ie ;k "1,?2 ";62 ga, qk} ezrxbjr vzrleljh o| BVCM"86* MB=M@)56* B?I, i` k Vbj`igj`j Cz`k M;2 miczg`";6 gg Ñ ?:6 gg# : ºg, kx k eciq rkxj ie =.: gC)gl` xi keeirh";= _,'1 "11 ga,. Mr|}xkccltkxli` erig 86* MB=M@)56* B?Ikeeirhjh k qblxj }iclh4 gv ;1<';2? ¶M> BVCM x _ , ;5.1 gl`>vzrlx| , <<.5*.

]|`xbj}l} ie ]kculhlul` K ";?k, k`h ]kculhlul` O ";?o,. K}iczxli` ie  ;k "=5:.: ga# 6.28: ggic, l` k glxzrj ie MB ?Mc? ) GjIB ";4;, ": gC, qk} }xlrrjh kx riig xjgvjrkxzrj eir 1 hk|} l`xbj vrj}j`mj ie }z`clabx. _jgiukc ie xbj }icuj`x z`hjr rjhzmjhvrj}}zrj keeirhjh k mrzhj gkxjrlkc qblmb qk} }jvkrkxjh o| rjvjkxjh

}lclmk ajc GVCM "jczj`x4 =* GjIB)MB?Mc?,. Z`rjkmxjh ;k "?61.6ga, qk} rjmiujrjh k} k qblxj }iclh# gv ?=5'?=< ¶M "clx.<#;6 gv?86'?8? ¶M,. Erkmxli } mi`xkl`l a ZU'kmxluj }vix} o| XCMk`kc|}l} qjrj miccjmxjh k`h jukvirkxjh xi hr|`j}}. Mr|}xkccltkxli`erig `'bjk`j)MB?Mc? "84;, akuj ;;.: ga "5.1*, ie ;?k# gv ?;?'

?;:¶

M "clx.=6

gv ?;1'???¶

M,# k`h =;.; ga ";2.?*, ie ;?o# gv?=6'?=8 ¶M "clx.=6 gv ?;5'??; ¶M, k} qblxj }iclh}. Xbj ;B k`h;=M }vjmxrk ie ;?k k`h ;?o l` MHMc= )MH=IH ";4;, qjrj lhj`xlmkcxi xbkx vrjuliz}c| rjvirxjh.=6

Mbrigkxiarkvblm ]jvkrkxli` ie ;=k k`h ;=o. Migviz`h :?5

";66 ga, qk} ezrxbjr }jvkrkxjh o| BVCM ^86* MB=M@)56* B?I"6.;* xrleczirikmjxlm kmlh l` B?I,W i` k Vbj`igj`j Cz`k M;2miczg` ";6 gg Ñ ?:6 gg# : ºg, kx k eciq rkxj ie = gC)gl` xikeeirh ;=k "=6 ga, k`h ;=o "?5 ga,.

"? ]#8k]#5k _#1 _#<]#;6k]#;6o _,'<'"Kmjx|ci|,'?'"?]#:]'hlgjxbi|'?#:'hlb|hriezrk`'='|c,hihjmkb|hri'5k#;6o'hlgjxb|c'8#;6'hlii'? B '`kvbxbi^?#;' mWv|rk '1'mkroi|clm kmlh gjxb|cj}xjr ";=k,4 ;B k`h ;=M @G_ "MHMc=,# }jj Xkocj ;> B_JLG]g )  t :6;.?=;? "mkcmh eir M?:B=8I;6Cl# :6;.?=?:,> BVCM x _ , =;.5gl`> vzrlx| , <<.8*.

"? ]#8k ]#5k _#1 _#<]#;6k]#;6o _,'<'"Kmjx|ci|,'?'"? _#:]'hlgjxbi|'?#:'hlb|hriezrk`'='|c,hihjmkb|hri'5k#;6o'hlgjxb|c'8#;6'hlii'? B '`kvbxbi^?#;' mWv|rk '1'mkroi|clm kmlh gjxb|cj}xjr ";=o,4 ;B k`h ;=M @G_ "MHMc=,# }jj Xkocj ;> B_JLG]g )  t :6;.?=;? "mkcmh eir M?:B=8I;6Cl# :6;.?=?:,> BVCM x _ , ==.8gl`> vzrlx| , <<.8*.

Mbrigkxiarkvblm ]jvkrkxli` ie ;8k k`h ;8o. Migviz`h 5?1

";?8 ga, qk} ezrxbjr }jvkrkxjh o| BVCM "=:* MB=M@)5:* B?I,i` k Vbj`igj`j Cz`k M;2 miczg` ";6 gg Ñ ?:6 gg# : ºg, kxk eciq rkxj ie 8 gC)gl` xi keeirh ;8k "86 ga, k`h ;8o "?= ga,.

"? ]#8k]#5k _#1 _#< ]#;6k]#;6o _,'<'"Kmjx|ci|,'?'"?]#:]'hlgjxbi|'?#= _#8#:'xjxrkb|hriezrk`'='|c,hihjmkb|hri'5k#;6o'hlgjxb|c'8#;6'hlii'? B '`kvbxbi^?#;' mWv|rk`'1'mkroi|clm kmlhgjxb|c j}xjr ";8k,4 ;B k`h ;=M @G_ "MHMc=,# }jj Xkocj ?>B_JLG] g )  t :6=.?85< "mkcmh eir M?:B=5I;6Cl# :6=.?85=,> BVCMx _ , ?8.2 gl`> vzrlx| , <2*.

"?]#8k ]#5k _#1 _#< ]#;6k]#;6o _,'<'"Kmjx|ci|,'?'"? _#: _'hlgjxbi|'?#= _#8#:'xjxrkb|hriezrk`'='|c,hihjmkb|hri'5k#;6o'hlgjxb|c'8#;6'hlii'? B '`kvbxbi^?#;' mWv|rk`'1'mkroi|clm kmlhgjxb|c j}xjr ";8o,4 ;B k`h ;=M @G_ "MHMc=,# }jj Xkocj ?>B_JLG] g )  t :6=.?85< "mkcmh eir M?:B=5I;6Cl# :6=.?85=,> BVCMx _ , ?1.< gl`> vzrlx| , <2*.

R'rk| Mr|}xkc ]xrzmxzrj ie ";= _,'1. ]l`acj'mr|}xkc R'rk|hleerkmxli` hkxk i` ";= _,'1 qjrj miccjmxjh kx ;6= N z}l`a Gi N_rkhlkxli` k`h k Orznjr KVJR LL MMH krjk hjxjmxir. K 6.62: Ñ

6.6<? Ñ 6.:1: gg= mr|}xkc qk} vrjvkrjh eir hkxk miccjmxli` o|mikxl`a qlxb blab'ul}mi}lx| glmri}mivj ilc "Vkrkxi`j'@# Bkgvxi`_j}jkrmb,. Xbj ilc'mikxjh mr|}xkc qk} giz`xjh i` k GlXjAj`GlmriGj}b giz`x "Glxjaj` CCM# Lxbkmk# @\, k`h xrk`}ejrrjhlggjhlkxjc| xi xbj mich }xrjkg ";6= N, i` xbj hleerkmxigjxjr. Xbjirxbirbigolm mr|}xkc qk} k `i`gjribjhrkc xql` l` }vkmj arizv

Xkocj 8. _j}zcx} erig ^=:]WAXV'ν'] Ez`mxli`kc K}}k| Mkrrljh izx l` ]xkoc| Xrk`}ejmxjh MBI Mjcc} Mi`xkl`l`a H@K eir Bzgk` º# θ# k`h δ

_jmjvxir}?5 k

N j " ]H# `G δ

migvh º θ δ JM:6 " ]J# `G J gko " ]J

;k @Hm @H @H 8: " ;6 ;62 " 88 @H @H @H :6 " ;6 ;68 " 8";= _,'1 l`kmxluj l`kmxluj @H 1:6 " 56 2; " 1;;k 8=6 " 26 l`kmxluj =56 " ;86 @H @H;;o ;:=6 " 186 8?=6 " ??66 :526 " ??26 @H @H;?k 156 " =?6 ?2=6 " =?6 886 " ;86 @H @H;=k ?=?6 " ;5:6 =?26 " ;586 <166 " ;666 @H @H;=o ?<=6 " ;666 ;?26 " ?16 ?=16 " ;?86 @H @H;8k ;=16 " 866 0;6#666 @H ?=:6 " 216 <: " :;8o l`kmxluj l`kmxluj l`kmxluj @H @H"','Z5<#:<= @H @H @H ?61 " =8 ;66 " ;:

k Xbj N j hkxk rjvrj}j`x xbj gjk` " ]H erig kx cjk}x xqi l`hjvj`hj`x hjxjrgl`kxli`} k`h xbj JM :6 k`h J gk hkxk rjvrj}j`x xbj gjk` " ]J erig kx cjk}xxbrjj l`hjvj`hj`x jvjrlgj`x}. J gk ukczj} qjrj migvkrjh z}l`a i`j'qk| K@IUK "Vrl}g u8# ArkvbVkh L`m.# ]k` Hljai# MK,. @i`j ie xbj J gk ukczj}qjrj }la`lelmk`xc| hleejrj`x erig xbkx ie Z5<#:<= kx v 3 6.6: "E;#;8 , ;.5:;> Hz``jxx“} xj}x,. o  J gk l} xbj vjrmj`x }xlgzckxli` ie ^=:]WAXV'ν'] ol`hl`arjckxluj xi xbj gklgzg }xlgzckxli` ie ol`hl`a io}jrujh qlxb Z5<#:<= rz` l` vkrkccjc qlxb xbj xj}x migviz`h}. m @ix hjxjrgl`jh.

 @jimcjrihk j Hlxjrvj j} erig ]kcUlk hlUl`irzg Dizr`kc ie Gjhlml`kc Mbjgl}xr|# ?661# Uic. :6# @i. ;: =56;

8/3/2019 Denise S. Simpson et al- Synthetic Studies of Neoclerodane Diterpenes from Salvia divinorum: Preparation and Opi…

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V?;?;?; qlxb z`lx mjcc hlgj`}li`} k , 5.=8?2"1, Ê# o , ;6.:5="?,Ê# m , =;.<5?"5, Ê. Mirrjmxli`} qjrj kvvcljh eir Cirj xt#vickrltkxli`# k`h ko}irvxli` jeejmx} z}l`a XQL@KO] u;.6: "OrznjrKR] L`m.# Gkhl}i # QL,. Hkxk }jcjmxjh eir z}j l` xbj el kcrjel`jgj`x qjrj `i`iujrckvvjh rjecjmxli`} erig xbj gkdir mig'vi`j`x ie xbj xql` k`h qjrj <<.5* migvcjxj xi ?<.16¶ β"kvvrilgkxjc| 6.1= Ê, qlxb k` kujrkaj rjhz`hk`m| arjkxjr xbk` 1vrlir xi gjral`a. Xbj }xrzmxzrj qk} }icujh o| hlrjmx gjxbih} k`hrjel`jh o| ezcc'gkxrl cjk}x'}{zkrj} i` E ? ukczj} z}l`a xbj vriarkg}eiz`h l` xbj ]BJCRXC }zlxj "Orznjr# ]BJCRXC u5.;8# ?666#

Orznjr KR] L`m.# Gkhl}i`# QL,. Vkrkgjxjr} rjel`jh l`mczhjh kxiglmmiirhl`kxj} k`h k`l}ixrivlm xbjrgkc vkrkgjxjr} eir kcc `i`'b|hriaj`kxig}. B|hriaj` kxig} i` mkroi`} qjrj l`mczhjh z}l`a k rlhl`agihjc "miirhl`kxj }blex} ie M kvvcljh xi B kxig}, qlxb M'Bhl}xk`mj }jx kx 6.<2 Ê. Xbj ko}iczxj mi`elazrkxli` qk} }jx i` xbjok}l} ie vrjuliz}c| hjxjrgl`jh }xrzmxzrj}. Kxiglm miirhl`kxj} eirmigviz`h 1 bkuj ojj` hjvi}lxjh qlxb xbj Mkgorlhaj Mr|}xkc'ciarkvblm Hkxk Mj`xrj "hjvi}lxli` `zgojr 5=21=6,. Mivlj} ie xbjhkxk mk` oj ioxkl`jh# erjj ie mbkraj# i` kvvclmkxli` xi MMHM# ;?Z`li` _ikh# Mkgorlhaj# MO? ;JT# ZN ^ek# .88"6,';??='==56==> j'gklc# hjvi}lxFmmhm.mkg.km.znW.

L` Ulxri Vbkrgkmicia|. Mjcc mzcxzrj# ^=:]WAXV'ν'] ol`hl`ak}}k|# k`h ^;?:LWLIR\ ol`hl`a k}}k|} vrimjjhjh k} hj}mrlojhjc}jqbjrj.?5#== Orljec|# rjmigol k`x MBI mjcc} "bGI_'MBI#bHI_'MBI# k`h bNI_'MBI, qjrj vrihzmjh o| }xkocj xrk`}ejm'

xli` qlxb xbj rj}vjmxluj bzgk` ivlilh rjmjvxir mH@K k`h vriulhjho| Hr. Ckrr| Xicc "]_L L`xjr`kxli`kc# MK,. Kcc hrza hlczxli` mzruj}krj gkhj zv qlxb ozeejr mi`xkl`l`a ; ga)gC O]K. ^;?:LWLIR\"5 ο'lihi'=#;8'hlb|hri|';1'm|mcivriv|cgjxb|c'8#: _'jvi|girvbl'`k`, "]K , ??66 Ml)ggic, qk} z}jh xi ckojc º# θ# k`h δ ol`hl`a}lxj}.== Xbj}j k}}k|} xiin vckmj l` :6 gG Xrl}'BMc# vB 1.8# qlxbk vrixjk}j l`blolxir mimnxklc ^okmlxrkml` ";66 ºa)gC,# oj}xkxl`";6 ºa)gC,# cjzvjvxl` "8 ºa)gC, k`h mb|gi}xkxl` "? ºa)gC,W# l`k el kc k}}k| uiczgj ie ;.6 gC. @i`}vjmlelm ol hl a qk}hjxjrgl`jh z}l`a ;6 ºG kcii`j. ]kcul`irl` K rjckxjh migviz`h}qjrj gkhj zv l` ;66* HG]I . ;6 gG ?'gjrmkvxijxbk`ic xivrihzmj k ;6 gG }iczxli`. Kcl{zix} ":6 ºC, ie xbl} }ximn }iczxli`qjrj vlvjxxjh l`xi gzcxlvcj glmriezaj xzoj} k`h }xirjh eritj` kx'26 ¶M. I` xbj hk| ie xbj k}}k|# k` kvvrivrlkxj `zgojr ie xzoj}qjrj xbkqjh k`h z}jh xi gknj zv hlczxli` mzruj}. K`| cjexiujr

migviz h qk} hl}mkrhjh.

Kmn`iqcjhagj`x. Xbl} qirn qk} }zvvirxjh o| @kxli`kcL`}xlxzxj} ie Bjkcxb# @kxli`kc L`}xlxzxj i` Hrza Koz}j Ark`xHK 6;2;:; "xi X.J.V., k`h \;'HK566? "xi D._.H., k`h l` vkrxo| xbj L`xrkgzrkc _j}jkrmb Vriarkg ie xbj @LB# @LHK.

]zvvirxl`a L`eirgkxli` Kuklckocj4 MLE elcj ie R'rk| hkxk eirmigviz`h ";= _,'1 k`h vzrlxlj} ie migviz h} ";= _,'1# ;=k# ;=o#;8k# k`h ;8o erig BVCM k`kc|}l}. Xbl} gkxjrlkc l} kuklckocj erjjie mbkraj ulk xbj L`xjr`jx kx bxxv4))vzo}.km}.ira.

_jejrj`mj}

";, Ukchj}# C. D.# LLL> Hlkt# D. C.> Vkzc# K. A. Jxb`ivbkrgkmicia| ie 

]nk'Gkrlk'Vk}xirk "]kculk# Hlul`irzg# Jvcl`a k`h Dkxluk'G,. D. Jxb`ivbkrgkmic. ;<2=# 1 # ?21'=;?.

"?, Ukchj}# C. D.# LLL.> Bkxeljch# A. G.> Nirjjhk# G.> Vkzc# K. A. ]xzhlj}ie ]kcUlk'hlUl`irzg " Ckglkmjkj,# k` Bkcczml`iaj`lm Gl`x erig xbj]ljrrk Gktkxjmk l` Ikkmk# Mj`xrkc Gjlmi. Jmi`iglm Oixk`| ;<21#8;# ?2='?<;.

"=, Ukchj}# C. D.# LLL. ]kcUlk hlUl`irzg k`h xbj Z`l{zj Hlxjrvj`jBkcczml`iaj`# ]kcul`irl` "Hlul`irl`, K. D V}|mbikmx. Hrza} ;<<8#?5 # ?11'?2=.

"8, ]ljojrx# H. D. ]kcUlk hlUl`irzg k`h ]kcul`irl` K}@jq Vbkrgkmi'cialmkc El`hl`a}. D. Jxb`ivbkrgkmic. ;<<8# 8=# :=':5.

":, ]bjeecjr# H. D.> _ixb# O. C. ]kcul irl K4 Xbj ‒Gkalm Gl x“Bkcczml`iaj` El`h} k Gicjmzckr Xkrajx l` xbj Nkvvk Ivlilh _jmjvxir.Xrj`h} Vbkrgkmic. ]ml. ?66=# ?8# ;61';6<.

"5, Hj``jb|# M. J.> X}izriz`l}# M.> Glccjr# K. J. Jukczkxli` ie BjrokcHljxkr| ]zvvcjgj`x} Gkrnjxjh i` xbj L`xjr`jx eir _jmrjkxli`kc Z}j.

 K``. Vbkrgkmixbjr. ?66:# =<# ;5=8';5=<.

"1, Ozmbjcjr# _.> Acjlxjr# M. B.> ]mbqijrjr# V.> Akjrx`jr# L. Z}j ie @i`vriblolxjh Bkcczml`iaj`lm Vck`x}4 L`mrjk}l`a _jcjuk`mj eirVzoclm Bjkcxb9 K Mk}j _jvirx k`h Clxjrkxzrj _juljq i` xbjMi`}zgvxli` ie ]kcUlk hlUl`irzg "Hlul`jr“} ]kaj,. Vbkrgkmiv}|'mblkxr| ?66:# =2# ;':.

"2, Qiciqlmb# Q. _.> Vjrnl`}# K. G.> Mlj`nl# D. D. K`kc|}l} ie xbjV}|mbikmxluj Xjrvj`ilh ]kcul`irl` K Mi`xj`x l` Eluj ]kcUlk hlUl'`irzg Bjrokc Vrihzmx}. Vbkrgkmixbjrkv| ?665# ?5 # ;?52';?1?.

"<, Irxjak# K.> Ociz`x# D. E.> Gk`mbk`h# V. ]. ]kcul`irl`# k @jq xrk`}'@jimcjrihk j Hlxjrvj`j erig ]kcUlk'hlUl`irzg " Ckolkxkj,. D. Mbjg.]im. Vjrnl` Xrk`}. ;<2?# ;# ?:6:'?:62.

";6, Ukchj}# C. D.# LLL> Ozxcjr# Q. G.> Bkxeljch# A. G.> Vkzc# K. A.>

Nirjjhk# G.> Hlul`irl`# K. k V}|mbixrivlm Xjrvj`ilh# k`h Hlul`irl`O erig xbj Bkcczml`iaj`lm Gjlmk` Gl`x ]kcUlk hlUl`irzg. D. Ira.Mbjg. ;<28# 8<# 81;5'81?6.

";;, Ukchj}# C. D.# LLL.> Mbk`a# B. G.> Ul}ajr# H. M.> Nirjjhk# G.]kcul`irl`# M# k @jq @jimcjrihk`j Hlxjrvj`j erig k OlikmxlujErkmxli` ie xbj Bkcczml`iaj lm Gjlmk` Gl`x ]kcUlk hlUl`irzg. Ira.

 Cjxx. ?66;# =# =<=:'=<=1.";?, Gz`ri# X. K.> _lttkmk}k# G. K.> ]kcul`irl`}# H'E. @jq @jimcjrihk`j

Hlxjrvj`ilh} erig ]kcUlk hlUl`irzg# k`h k` Lgvriujh Gjxbih eirxbj L}ickxli` ie ]kcul`irl` K. D. @kx. Vrih. ?66=# 55 # 16='16:.

";=, Olabkg# K. N.> Gz`ri# X. K.> _lttkmk}k# G. K.> _iol`}'Oriq`j#_. G.> Hlul`kxirl`}# K'M. @jq @jimcjrihk`j Hlxjrvj`ilh} erigxbj Mi`xriccjh ]kaj ]kcUlk hlUl`irzg. D. @kx. Vrih. ?66=# 55 # ;?8?';?88.

";8, Bkrhl`a# Q. Q.> Xlhajqjcc# N.> ]mbglhx# G.> ]bkb# N.> Hjr}mb# M.G.> ]`|hjr# D.> Vkrrl}b# H.> Hj}mbkgv}# D. _.> _ixbgk`# _. O.>Vrl}l`tk`i# X. J. ]kcul`lml`} K k`h O# @jq @jimcjrihk`j Hlxjrvj j}erig ]kcUlk hlUl`irzg. Ira. Cjxx. ?66:# 1 # =6;1'=6?6.

";:, Cjj# H. \.> Gk# T.> Clz'Mbj`# C. \.> Qk`a# \.> Mbj`# \.> Mkrcjti`#Q. K.# Dr.> Mibj`# O. @jq @jimcjrihk`j Hlxjrvj`ilh} L}ickxjh erigxbj Cjkuj} ie  ]kcUlk hlUl`irzg k`h Xbjlr Ol`hl`a Keel`lxlj} eirBzgk` Nkvvk Ivlilh _jmjvxir}. Oliira. Gjh. Mbjg. ?66:# ;=#:5=:':5=<.

";5, _ixb# O. C.> Ok`jr# N.> Qj}xnkjgvjr# _.> ]ljojrx# H.> _lmj# N. M.>]xjl`ojra# ].> Jr`}ojrajr# V.> _ixbgk`# _. O. ]kcul`irl` K4 K Vixj`x@kxzrkcc| Immzrrl`a @i``lxriaj`iz} Nkvvk Ivlilh ]jcjmxluj Kai`l}x.Vrim. @kxc. Kmkh. ]ml. Z.].K. ?66?# <<# ;;<=8';;<=<.

";1, Uirxbjrg}# X. K.> _ixb# O. C. ]kcul`irl` K4 Erig @kxzrkc Vrihzmxxi Bzgk` Xbjrkvjzxlm}. Gic. L`xjr U. ?665# 5 # ?:1'5:.

";2, Mkrcjti`# Q. K.# Dr.> Ojazl`# M.> Hl`ljrl# D. K.> Okzgk``# G. B.>_lmbkrh}# G. _.> Xihxj`nive# G. ].> _ixbgk`# _. O.> Gk# T.> Cjj#H. \.> Mibj # O. G. Hjvrj}}luj'Clnj Jeejmx} ie xbj δ'Ivlilh_jmjvxir Kai`l}x ]kcul`irl` K i` Ojbkulir k`h @jzrimbjgl}xr| l`_kx}. D. Vbkrgkmic. Jv. Xbjr. ?665# =;5 # 886'881.

";<, Ek`xjari}}l# Q. J.> Nzacj# N. G.> Ukchj}# C. D.# =rh.> Nirjjhk# G.>Qiih}# D. B. Nkvvk'Ivlilh _jmjvxir'Gjhlkxjh Jeejmx} ie xbj Vck`x'Hjrlujh Bkcczml`iaj`# ]kcul`irl` K# i` L`ujrxjh ]mrjj` Vjreirgk`mjl` xbj Giz}j. OjbkU. Vbkrgkmic. ?66:# ;5 # 5?1'5==.

"?6, Hk`ljck# O.> Ukcjrlk# C.> ]lgi k# V.> Kcj}}lk# T.> Mblkrk# A.'_.> J`ti#A.> Gkrlkjcul`k# ]. Bkcczml`kxir| k`h _jqkrhl`a Jeejmx ie ]kcul`irl`K l` Tjorkel}b4 δ'Ivlilh k`h MO;'Mk``kol`ilh _jmjvxir L`uicuj'gj`x. V}|mbivbkrgkmicia| ?661# ;<6# 88;'882.

"?;, Bkrhl`a# Q. Q.> Xlhajqjcc# N.> O|rh# @.> Mioo# B.> Hjr}mb# M. G.>Ozxjcgk`# J. _.> _ixbgk`# _. O.> Vrl}l`tk`i# X. J. @jimcjrihk`jHlxjrvj`j} k} k @iujc ]mkeeich eir gz Ivlilh _jmjvxir Clak`h}. D.

  Gjh. Mbjg. ?66:# 82# 815:'811;."??, GmMzrh|# M. _.> ]zenk# N. D.> ]glxb# A. B.> Qkr`lmn# D. J.> @ljxi#

G. D. K`xl`imlmjvxluj Vrielcj ie ]kcul`irl` K# k ]xrzmxzrkcc| Z`l{zjNkvvk Ivlilh _jmjvxir Kai`l}x. Vbkrgkmic. Olimbjg. OjbkU. ?665#2=# ;6<';;=.

"?=, Dib`# X. E.> Erj`mb# C. A.> Jrclmbgk`# D. ]. Xbj K`xl`imlmjvxluj Jeejmxie ]kcul`irl` K l` Glmj. Jzr. D. Vbkrgkmic. ?665# :8:# ;?<';==.

"?8, K`}i iee# G. K.> Tbk`a# D.> Mt|t|n# X.> _ixbgk`# _. O.> ]xjqkrx#D.> Rz# B.> Tdqli`|# D.> ]ljojrx# H. D.> \k`a# E.> _ixb# O. C.> Vl`xkr#D. J. K`xl`imlmjvxluj k`h B|vixbjrglm Jeejmx} ie ]kcul`irl` K KrjKoicl}bjh l` k @iujc ]xrkl` ie δ'Ivlilh _jmjvxir'; N`imnizx Glmj.

  D. Vbkrgkmic. Jv. Xbjr. ?665# =;2# 58;'582."?:, Xlhajqjcc# N.> Bkrhl`a# Q. Q.> ]mbglhx# G.> Bichj`# N. A.> Gzrr|#

H. D.> Vrl}l`tk`i# X. J. K Ekmlcj Gjxbih eir xbj Vrjvkrkxli` ie Hjzxjrlzg Ckojcjh ]kcul`irl` K4 ]|`xbj}l} ie ^?#?#?'?B=W']kcul`irl`K. Oliira. Gjh. Mbjg. Cjxx. ?668# ;8# :6<<':;6?.

"?5, Bkrhl`a# Q. Q.> ]mbglhx# G.> Xlhajqjcc# N.> Nk``k`# V.> Bichj`#N. A.> Alcgizr# O.> @kukrri# B.> _ixbgk`# _. O.> Vrl}l`tk`i# X. J.]|`xbjxlm ]xzhlj} ie @jimcjrihk`j Hlxjrvj`j} erig ]kcUlk hlUl'`irzg4 ]jgl}|`xbj}l} ie ]kcul`lml`} K k`h O k`h Ixbjr MbjglmkcXrk`}eirgkxli`} ie ]kcul`irl` K. D. @kx. Vrih. ?665# 5<# ;61';;?.

"?1, Bkrhl`a# Q. Q.> ]mbglhx# G.> Xlhajqjcc# N.> Nk``k`# V.> Bichj`#N. A.> Hjr}mb# M. G.> _ixbgk`# _. O.> Vrl}l`tk`i# X. J. ]|`xbjxlm]xzhlj} ie @jimcjrihk`j Hlxjrvj`j} erig ]kcUlk hlUl`irzg4 ]jcjmxlujGihlelmkxli` ie xbj Ezrk` _l`a. Oliira. Gjh. Mbjg. Cjxx. ?665# ;5 #=;16'=;18.

=56? Dizr`kc ie Gjhlml`kc Mbjgl}xr|# ?661# Uic. :6# @i. ;: ]lgv}i` jx kc.

8/3/2019 Denise S. Simpson et al- Synthetic Studies of Neoclerodane Diterpenes from Salvia divinorum: Preparation and Opi…

http://slidepdf.com/reader/full/denise-s-simpson-et-al-synthetic-studies-of-neoclerodane-diterpenes-from 9/9

"?2, Gz`ri# X. K.> _lttkmk}k# G. K.> _ixb# O. C.> Xixb# O. K.> \k`# E.]xzhlj} xiqkrh xbj Vbkrgkmivbirj ie ]kcul`irl` K# k Vixj`x NkvvkIvlilh _jmjvxir Kai`l}x. D. Gjh. Mbjg. ?66:# 82# =8:'=82.

"?<, Njr`k`# G. _.> Ekzcn`jr# H. D. _jali}jcjmxluj Ilhkxli` ie ='Kcn|'cezrk`} xi ='Kcn|c'8'b|hri|ozxj`iclhj}. D. Ira. Mbjg. ;<22# :=#?11='?115.

"=6, ]blrixk# I.> @kakgkx}z# N.> ]jnlxk# ]. @ji'mcjrihk`j Hlxjrvj`j} erigxbj Bkcczml`iaj`lm ]kaj ]kcUlk hlUl`irzg. D. @kx. Vrih. ?665# 5<#;12?';125.

"=;, Rz# B.> Bk}blgixi# K.> _lmj# N. M.> Dkmio}i`# K. J.> Xbigk}# D. O.>Mkrricc# E. L.> Ckl# D.> _ixbgk`# _. O. Ivlilh Vjvxlhj _jmjvxir ]xzhlj}.;8. ]xjrjimbjgl}xr| Hjxjrgl`j} Kai l}x Jeelmkm| k`h L`xrl }lm

Jeelmkm| l` xbj ^=:]WAXV'ν'] Ez`mxli`kc Ol`hl`a K}}k|. ]|`kv}j?66;# =<# 58'5<.

"=?, ]mbq|tjr# _. L` ]jkrmb ie xbj ‒Oli'kmxluj Mi`eirgkxli`“}L} LxL`hzmjh o| xbj Xkrajx Mjcc Gjgork`j. D. Gic. _jmia`lx. ;<<:# 2#='2.

"==, _ixbgk`# _. O.> Gzrvb|# H. C.> Rz# B.> Aihl`# D. K.> Hjr}mb# M.G.> Vkrxlcck# D. ].> Xlhajqjcc# N.> ]mbglhx# G.> Vrl}l`tk`i# X. J.

]kcul irl` K4 Kcci}xjrlm L`xjrkmxli`} kx xbj º'Ivlilh _jmjvxir. D.

Vbkrgkmic. Jv. Xbjr. ?661# =?6# 26;'2;6."=8, hj Mi}xk# O. _.> Lkhkrick# G. D.> _ixbgk`# _. O.> Ojrgk`# N. E.>

Ajiraj# M.> @jqgk`# K. B.> Gkboizol# K.> Dkmio}i`# K. J.> _lmj#N. M. Vrioj} eir @krmixlm _jmjvxir Gjhlkxjh Vbj`igj k. ;2.Jvlgjrlm 5_' k`h 5 ο'Lihi'=#;8'hlb|hri|';1'"m|mcivriv|cgjxb|c,'8#:_'jvi|girvbl`k`} k} Vixj`xlkc Clak`h} eir Ivlilh _jmjvxir]l`acj Vbixi` Jgl}}li` Migvzxjh Xigiarkvb| "]VJMX,4 ]|`xbj}l}#Jukczkxli`# k`h _khlimbjgl}xr| ie ^;?:LW'5 ο'Lihi'=#;8'hlb|hri|';1'"m|mcivriv|cgjxb|c,'8#:_'jvi|girvbl`k` "^;?:LWLIR\,. D. Gjh.

Mbjg. ;<<?# =:# ?2?5'?2=:.

"=:, @l# [.> Rz# B.> Vkrxlcck# D. ].> hj Mi}xk# O. _.> _lmj# N. M.> _ixbgk`#_. O. ]jcjmxluj Ckojcl`a ie δ? Ivlilh _jmjvxir} l` _kx Orkl` o|^;?:LWLIR\4 L`xjrkmxli` ie Ivlilh Vjvxlhj} k`h Ixbjr Hrza} qlxbGzcxlvcj δ?k Ol`hl`a ]lxj}. Vjvxlhj} ;<<=# ;8# ;?1<';?<=.

DG616=<=H

 @jimcjrihk`j Hlxjrvj`j} erig ]kcUlk hlUl`irzg Dizr`kc ie Gjhlml`kc Mbjgl}xr|# ?661# Uic. :6# @i. ;: =56=