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Annulation of β-aryl-α-nitro-α,β−enals and 2,2-dimethyl-1,3-dioxan-5-one: a one-step
assembly of nitrocyclitols. Application to a short practical synthesis of (+/-)-7-deoxy-2-
epi-pancratistatin tetraacetate
Juan Carlos Ortiz,† Lidia Ozores,‡ Fernando Cagide, Ricardo Alonso*
Departamento de Química Orgánica, Universidade de Santiago, 15782 Santiago de Compostela, Spain
Supporting Information qoraa@u
† Currently at Sintenovo, Mexico. ‡ Currently at the Max Planck Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, D-45470 Mülheim an der Ruhr, Germany
S1
ppm (f1)0.01.02.03.04.05.06.07.08.0
NO2
OH
OO
O
O
H
S2
ppm (f1)050100150200
NO2
OH
OO
O
H
O
S3
ppm (t1)0.01.02.03.04.05.06.07.08.0
NO2
OH
OO
O
HO
O
S4
ppm (t1)050100150200
O
O NO2
OH
OO
OH
S5
ppm (t1)050100150200
NO2
OH
OO
O
HO
O
S6
ppm (f1)0.01.02.03.04.05.06.07.08.0
O
O NO2
OH
OO
OH
OMe
S7
ppm (t1)050100150200
NO2
OH
OO
O
HO
O
OMe
S8
ppm (t1)050100150200
NO2
OH
OO
O
HO
O
OMe
S9
ppm (t1)0.01.02.03.04.05.06.07.08.0
NO2
OH
OO
O
H
O
S10
ppm (t1)050100150200
NO2
OH
OO
O
H
O
S11
ppm (f1)050100150200
NO2
OH
OO
O
H
O
S12
ppm (t1)0.01.02.03.04.05.06.07.08.0
HNO
OO
O
HO
OO
MeO
S13
ppm (t1)050100150200
HNO
OO
O
HO
OO
MeO
S14
ppm (t1)050100150200
HNO
OO
O
HO
OO
MeO
S15
ppm (t1)0.01.02.03.04.05.06.07.08.0
HNOAc
OAcOAc
AcO
HO
OO
MeO
S16
ppm (t1)050100150200
HNOAc
OAcOAc
AcO
HO
OO
MeO
S17
ppm (t1)050100150200
HNOAc
OAcOAc
AcO
HO
OO
MeO
S18
ppm (t1)1.02.03.04.05.06.07.08.0
NHOAc
OAcOAc
AcO
HO
O
O
S19
ppm (t1)050100150200
NHOAc
OAcOAc
AcO
HO
O
O
S20
ppm (t1)050100150200
NHOAc
OAcOAc
AcO
HO
O
O
S21
