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The 7th CCS‐CSJ Young Chemists Forum 2017 

―Frontier in Organic Synthesis toward Middle Molecular Strategy 

The Chemical Society of Japan    The 97th Annual Meeting 

 ■Date  March 18th (Saturday), 2017    9:00‐17:40 ■Venue  S2; Room J24,    House B, Bldg. 4,   

Hiyoshi Campus, Keio University, Yokohama, Kanagawa, Japan ■Hosted by The Chemical Society of Japan & The Chinese Chemical Society 

 09:00  Opening Remarks  Representative from CSJ 

Hisashi Yamamoto President of the CSJ 

 

09:05  Introductory Talk  Koichi Fukase,   Osaka University 

…2 

09:10  Aromatic Molecules: Decarbonylative Coupling and Multiple Arylation   

Junichiro Yamaguchi, Waseda University 

…3 

09:40  C‐H Functionalization Strategy for Chemical Synthesis of α‐Amino Acids and Complex Peptides   

Gong Chen,   Nankai University 

…5 

10:10  Coffee break 

10:20  Synthesis  and  Biological  Evaluation  of  Antibiotic Polyketides 

Yoko Saikawa,   Keio University 

…7 

10:50  Natural Product Synthesis Facilitated by Ligand Design  Wenjun Tang,   Shanghai Institute of Organic Chemistry   

…9 

11:20  Synthesis of Monomers for Spectomycin B1,   A Middle Size SUMOylation Inhibitor Molecule 

Go Hirai,   Kyushu University 

…11 

11:50  Lunch 

13:10  Remote  Activation  of  O/S‐Benzyl  Glycosides  in Latent‐Active Glycosylation 

Qian Wan,   Huazhong Univ. of Science and Technology 

…13 

13:40  Development  of  the  Novel  Cancer  Immunotherapy Utilizing α‐Gal 

Yoshiyuki Manabe, et al. Osaka University 

…15 

14:10  Type II Intramolecular [5+2] Cycloaddition  Chuang‐Chuang Li,   South Univ. of Science & Technology of China 

…17 

14:40  Coffee break 

14:50  Aryl  Fluorides:  a  Versatile  Synthetic  Platform  for Natural Product Synthesis 

Ken Ohmori,   Tokyo Institute of Technology 

…19 

15:20  Total  Synthesis  of  Bioactive  Natural  Products: Efficiency and Diversity 

Shuanhu Gao,   East China Normal University 

…21 

15:50  Coffee break 

16:00  Development of Chemical Assembly Lines Generating Skeletally Diverse Natural Products and Their Variants 

Hiroki Oguri,   Tokyo Univ. of Agriculture and Technology   

…23 

16:30  Complex  Natural  Product  as  a  Driving  Force  for Discovery in Organic Synthesis and Chemical Biology 

Xiaoguang Lei,   Peking University 

…25 

17:00  Closing Remarks  

Representative from CCS Biao Yu     Shanghai Institute of Organic Chemistry 

…13 

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FRONTIER IN ORGANIC SYNTHESIS TOWARD MIDDLE MOLECULAR STRATEGY  4 

Aromatic Molecules:

Decarbonylative Coupling and Multiple Arylation

Junichiro Yamaguchi Department of Applied Chemistry, Waseda University,

3-4-1 Ohkubo, Shinjuku, Tokyo 169-8555, Japan

In recent years, catalytic decarbonylative coupling reactions using aromatic esters as aryl electrophiles have been studied to produce various transformations. We report the development of catalytic decarbonylative transformations of aromatic esters, which are C–H arylation of azoles, Suzuki–Miyaura coupling, alkynylation, and intramolecular etherifications under the influence of Pd or Ni catalysts. The key for these achievements was newly developed catalytic systems in which our unique ligand was employed (Figure 1A). By utilization of these reactions, we successfully achieved applications such as the formal synthesis of naturally occurring compounds.

Meanwhile, multiply arylated aromatics have often been found in natural products, pharmaceuticals and functional organic materials. We achieved the programmed synthesis of multiply arylated aromatics using sequential C–H couplings, cross couplings, and Diels–Alder reaction of thiophene S-oxides. This synthetic method can provide hexaarylbenzenes, pentaarylpyridines, multiply arylated naphthalenes, and a multiply arylated anthracene bearing different aryl groups (Figure 1B).

I would like to talk about above two topics about transformation of aromatic molecules in this symposium.

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FRONTIER IN ORGANIC SYNTHESIS TOWARD MIDDLE MOLECULAR STRATEGY  6 

C－H Functionalization Strategy for Chemical Synthesis of -Amino Acids and Complex Peptides

Gong Chen State Key Laboratory of Elemento-Organic Chemistry, Nankai University,

Tianjin, 300071, P. R. China

-Amino acids (AA) are one of the most useful chiral building blocks for synthesis. Despite

significant advances in synthetic methodology, the efficient synthesis of enantiopure AAs carrying complex side chains, as seen in numerous peptide natural products, remains challenging. Complementary to the conventional synthetic strategies, a strategy based on the selective functionalization of side chain C−H bonds, particularly sp3 hybridized C−H bonds, of various readily available AA precursors may provide a more straightforward and broadly applicable means for the synthesis and transformation of AAs. Over the past few years, we have carried out systematic investigation of palladium-catalyzed bidentate auxiliary-directed C−H functionalization reactions for AA substrates. Our strategies utilize two different types of amide-linked auxiliary groups, attached at the N or C terminus of AA substrates, to exert complimentary regio- and stereo-control on C−H functionalization reactions through palladacycle intermediates. A variety of AA precursors can undergo multiple modes of C(sp3)−H functionalization, including arylation, alkenylation, alkynylation, alkylation, alkoxylation and intramolecular aminations, at the , and even positions to form new AA products with diverse structures. In addition to transforming AAs at previously unreachable positions, these palladium-catalyzed C−H functionalization strategies enable new retrosynthetic logic for the synthesis of many basic AAs from a common alanine precursor. This approach reduces the synthetic difficulty for many AAs by bypassing the requirement for stereocontrol at C, and relies on straightforward and convergent single-bond coupling transformations at the -methyl position of alanine to access a wide range of -mono-substituted AAs. Moreover, these -mono-substituted AAs can undergo further C−H functionalization at the -methylene position to generate various -branched AAs in a stereoselective and programmable fashion. These new strategies offer readily applicable methods for synthesis of challenging AAs and facilitate the efficient total synthesis of complex peptide natural products.

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FRONTIER IN ORGANIC SYNTHESIS TOWARD MIDDLE MOLECULAR STRATEGY  8 

Synthesis and Biological Evaluation of Antibiotic Polyketides

Yoko Saikawa Department of Applied Chemistry, Faculty of Science and Technology, Keio University

3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan

There are a variety of polyketides with complex structure and fascinating bioactivities. We are focusing on the synthesis of such attractive natural products to develop new strategy useful for their syntheses and to reveal the substructure requisite for their bioactivities.

Ansa-type antibiotic kendomycin (1) has a unique quinone methide architecture connected to a highly-substituted tetrahydropyran ring and possesses potent antibacterial and cytotoxic activities. 1 was synthesized via intramolecular Dötz reaction which enabled simultaneous aromatization and macrocyclization. Using this efficient method to construct an ansa-skeleton, new ansa-type analogs were also synthesized. Antimicrobial activities of the analogs revealed necessity of the ansa-skeleton.

On the other hand, total synthesis of lactonamycin (2), a potent antimicrobial polyketide, was performed via sequential construction of its six rings followed by glycosylation. In the course of the synthesis, we developed a new method for construction of isoindolinone moiety (A-ring), that is modified Bischler-Napieralski reaction. Various model compounds and synthetic intermediates of 2 provided insight into the biological function of its complex structure which is dug down to the individual factors such as -lactam (A-ring), EF-ring configuration, and the rhodinose linkage.

The latest topic of a cytotoxic naphthofuranoxepin dioscorealide A (3) consists of its intriguing structural feature and investigation of its asymmetric synthesis via chiral transcription of the synthetic intermediate into 3 with mobile chiral center.

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FRONTIER IN ORGANIC SYNTHESIS TOWARD MIDDLE MOLECULAR STRATEGY  10 

Natural Product Synthesis Facilitated by Ligand Design

Wenjun Tang State Key Laboratory of Bio-Organic & Natural Products Chemistry, Shanghai Institute

of Organic Chemistry, Shanghai 200032, P.R.China

The asymmetric intramolecular Heck reaction have become one of most successful

method for constructing polycyclic skeletons bearing an all-carbon chiral quaternary center in natural product synthesis. Despite its versatile synthetic utilities, the asymmetric Heck cyclization employs an olefinic starting material which often requires multiple synthetic steps to prepare. In addition, the transformation of its olefinic product to a target molecule is sometimes tedious. An attractive alternative is enantioselective intramolecular dearomative cyclization which employs an often more accessible substrate with an aryl moiety and leads to a multicyclic product bearing an all-carbon quaternary center. Because of the closer resemblance of the cyclic product to a variety of chiral natural products, this method offers advantages over the Heck reaction for the synthesis of a number of chiral polycyclic natural products. The key issue is how to achieve satisfactory reactivity, chemoselectivity, and enantioselectivity by employing an effective chiral ligand. Herein we described the ligand design that have enabled an effective dearomative cyclization and the efficient asymmetric synthesis of several biologically important alkaloids and polyketides.

Figure 1. Polycyclic natural products

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FRONTIER IN ORGANIC SYNTHESIS TOWARD MIDDLE MOLECULAR STRATEGY  12 

Synthesis of Monomers for Spectomycin B1,

A Middle Size SUMOylation Inhibitor Molecule

Go Hirai,a,b Yusaku Nomura,b Frederic Thuaud,b Daisuke Sekine,b and Mikiko Sodeokab aGraduate School of Pharmaceutical Sciences, Kyushu University, 3-1-1 Maidashi,

Higashi-ku, Fukuoka 812-8582, Japan bRIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan

Spectomycin B1 (SMB1) was isolated from streptomyces spectabilis in 1994, and its monomeric homolog, spectomycin A1 (SMA1) and A2 (SMA2), were also identified at the same time.1 Our collaborators Dr. It and Dr. Yoshida recently reported that SMB1 exhibited the inhibitory activity for protein SUMOylation, through direct binding to SUMO-conjugating enzyme E2.2

Protein SUMOylation is one of the post-translational modification, in which lysine residue on substrate protein is modified by small ubiquitin-like modifier (SUMO). Dysregulation of SUMOylation pathway is involved in several diseases, and upregulation of enzymes related to SUMOylation was observed in several cancers. Thus, SUMOylation inhibitors would be useful as tools to understand the precise role of SUMOylation as well as candidates for therapeutic agents.

Although the dimeric structure was shown to be requisite for its anti-microbial activity,1 the effect of SMAs for protein SUMOylation has not been clarified yet due to the unavailability of materials. Furthermore, relative and absolute stereochemistry of SMAs and SMB1 remains to be determined. This time, we synthesized all possible stereoisomers of SMA1 and SMA2, in order to confirm their absolute structures as well as the importance of dimeric structure of SMB1 on inhibitory activity for protein SUMOylation.

We would like to thank Ms. Satoko Maeda, Dr. Akihiro Ito, and Prof. Minoru Yoshida for conducting biochemical experiments. We also thank Dr. Hiroyuki Koshino for NMR measurement, Dr. Daisuke Hashizume for X-ray crystallographic analysis, and Mr. Thomas Cruchter for his kind support.

Figure 1. Structures of SMB1, SMA1, and SMA2

References 1. Staley, A. L.; Rinehart, K. L. J. Antibiot. 1994, 47, 1425-1433. 2. Hirohama, M.; Kumar, A.; Fukuda, I.; Matsuoka, S.; Igarashi, Y.; Saitoh, H.; Takagi, M.;

Shin-ya, K.; Honda, K.; Kondoh, Y.; Saito, T.; Nakao, Y.; Osada, H.; Zhang, K. Y.; Yoshida, M.; Ito, A. ACS Chem. Biol. 2013, 8, 2635-2642.

13  7th CCS/CSJ Young Chemists Forum 

Qian Wan Professor of Chemistry School of Pharmacy, Huazhong University of Science and Technology Address: Hangkong Road 13, Wuhan, Hubei, China Tel & Fax: (+86)-13971060097 E-mail: wanqian@hust.edu.cn

Educational Background 1997 B.Sc., Central China Normal University 1999 M.Sc., Paris-Sud (XI) University (supervisor: Prof. Claudine Augé) 2004 Ph.D., Paris-Sud (XI) University (supervisor: Prof. André Lubineau)

Professional Career 2004 Research Fellow, Memorial Sloan-Kettering Cancer Center, New York, NY, USA

(Advisor: Prof. Samuel J. Danishefsky) 2007 Scientist, Department of Medicinal Chemistry, Amgen Inc., Cambridge, MA, USA 2012 Professor, School of Pharmacy, Huazhong University of Science and Technology 2014 Vice Dean of School of Pharmacy

Research Interests 1) Carbohydrate Chemistry 2) Free Radical Chemistry

Awards 2017 Asian Core Program Lectureship Award (to Taiwan) 2017 Asian Core Program Lectureship Award (to Singapore) 2015 7th Asian Community of Glycoscience and Glycotechnology Conference Best Poster

Award, Miyagi, Japan 2012 “Thousand Talents Program” Young Investigator Award 2011 Amgen First Green Chemistry in Medicinal Chemistry Award

Recent Publications 1. "Remote Activation of Disarmed Thioglycosides in Latent-Active Glycosylation via Interrupted

Pummerer Reaction", Xiao, X.; Zhao, Y.; Shu, P.; Zhao, X.; Liu, Y.; Sun, J.; Zhang, Q.; Zeng, J.; Wan,

Q.* J. Am. Chem. Soc. 2016, 138, 13402. 2. "Glycosylation via Remote Activation of Anomeric Leaving Groups: Development of

2-(2-Propylsulfinyl)benzyl Glycosides as Novel Glycosyl Donors", Org. Chem. Front. 2016, 3, 177. 3. "Interrupted Pummerer Reaction in Latent-Active Glycosylation: A Novel Type of Glycosyl Donors

with Recyclable and Regenerative Leaving Group", Angew. Chem. Int. Ed. 2015, 54, 14432. 4. "Selective S-deacetylation Inspired by Native Chemical Ligation: Practical Syntheses of Glycosyl

Thiols and Drug Mercapto-analogues", Shu, P.; Zeng, J.; Tao, J.; Zhao, Y.; Yao, G.; Wan, Q.* Green

Chem. 2015, 17, 2545. 5. "Stereoselective Synthesis of α-linked 2-Deoxy Glycosides Enabled by Visible Light Mediated

Reductive Deiodination", Wang, H.; Tao, J.; Cai, X.; Chen, W.; Zhao, Y.; Xu, Y.; Yao, W.; Zeng, J.; Wan,

Q.* Chem. Eur. J. 2014, 20, 17319.

FRONTIER IN ORGANIC SYNTHESIS TOWARD MIDDLE MOLECULAR STRATEGY  14 

Remote Activation of O/S-Benzyl Glycosides in Latent-Active Glycosylation

Xiong Xiao, Yueqi Zhao, Yang Xu, Jianchang Sun, Jing Fang, Xiang Zhao, Yan Liu, Lingkui Meng, Jing Zeng and Qian Wan*

School of Pharmacy, Huazhong University of Science and Technology, Wuhan, Hubei, P. R. China

Latent O/S-glycosides, O/S-2-(2-propylthiol)benzyl (PTB) glycosides, were converted into the corresponding active glycosyl donors, O/S-2-(2-propylsulfinyl)benzyl (PSB) glycosides, by a simple and efficient oxidation. Treatment of PSB donors and various acceptors with triflic anhydride provided the desired glycosides in good to excellent yields. Three natural hepatoprotective glycosides, Leonuriside B, Leonoside E and F, were synthesized efficiently in a convergent [3+1] manner with this newly developed methods. The total syntheses also led to structural revisions of these phenylethanoid glycosides.

Figure 1. Interrupted Pummerer reaction mediated glycosylation

15  7th

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FRONTIER IN ORGANIC SYNTHESIS TOWARD MIDDLE MOLECULAR STRATEGY  18 

Type II Intramolecular [5+2] Cycloaddition

Chuang-Chuang Li* Department of Chemistry, South University of Science and Technology of China,

Shenzhen 518055, P. R. China

Developing efficient reactions for achieving bridged ring systems is a long-standing

challenge but very significant in organic chemistry, considering that such motif is widely

found in natural products (such as Taxol®) with significant biological activities. So far there

are no general reactions available for the single-step synthesis of bridged

seven-membered-ring systems efficiently. Here, we describe the first type II intramolecular

[5+2] cycloaddition reaction,1 which allows the efficient and diastereoselective construction

of various highly functionalized and synthetically challenging bridged seven-membered ring

systems. This simple, thermal transformation has shown a broad substrate scope and is high

yielding, with high functional group tolerance and unique endo selectivity. The highly strained

tricyclic cores of ingenol mebutate (Picato®) and cyclocitrinol are synthesized efficiently and

diastereoselectively using this methodology.

Reference 1. (a) Mei, G.; Liu, X.; Qiao, C.; Chen, W.; Li, C.-C. Angew. Chem. Int. Ed. 2015, 54, 1754. (b) Mei, G.; Yuan,

H.; Gu, Y.; Chen, W.; Chung, L.; Li, C.-C. Angew. Chem. Int. Ed. 2014, 53, 11051.

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FRONTIER IN ORGANIC SYNTHESIS TOWARD MIDDLE MOLECULAR STRATEGY  20 

Aryl Fluorides, a Versatile Synthetic Platform for Natural Product Synthesis

Ken Ohmori Department of Chemistry, School of Science, Tokyo Institute of Technology

O-okayama, Meguroku, Tokyo 152-8551, Japan

Organofluorine compounds often show unusual chemical properties and behavior in organic reactions. Among them, fluoroaromatic compounds（aryl fluorides) serve great potential as versatile building blocks for synthesis of complex molecules. In this symposium, the author will present some utilities of aryl fluorides in natural product synthesis, where SNAr reaction and ortho-metalation/alkylation sequences are subjected as a key transformation. Details will be discussed in this presentation.

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FRONTIER IN ORGANIC SYNTHESIS TOWARD MIDDLE MOLECULAR STRATEGY  22 

Total Synthesis of Bioactive Natural Products: Efficiency and Diversity

Shuanhu Gao Shanghai Key Laboratory of Green Chemistry and Chemical Processes,

School of Chemistry and Molecular Engineering, East China Normal University, 3663 Zhongshan N Rd, HuaShiDa, Putuo Qu, Shanghai, P. R. China 200062

The chemical synthesis of structurally interesting and biologically relevant natural products has served as a driving force for developing new methodologies, testing the scope of existing synthetic methods. It also provides the platform for the further identification of their specific biological targets and mechanistic mode of action. Our research interests are devoted to develop synthetic useful methodologies to address natural target molecules that have novel molecular structure, potent biological activity, and the potential for mechanistic studies.

In this presentation, I will introduce our recent progress in the total synthesis of hamigerans, and structurally related natural products. A newly developed photo-induced enolization/Diels–Alder strategy and its synthetic applications in the synthesis of cordiachrome and anthrabenzoxocinone type natural products will also be discussed.

Figure 1. Target Molecules

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FRONTIER IN ORGANIC SYNTHESIS TOWARD MIDDLE MOLECULAR STRATEGY  24 

Development of Chemical Assembly Lines

Generating Skeletally Diverse Natural Products and Their Variants

Hiroki Oguria,b aDepartment of Applied Chemistry, Graduate School of Engineering, Tokyo University of

Agriculture and Technology, 2-24-16 Nakacho, Koganei, Tokyo 184-8588, Japan bJST-PRESTO, 4-1-8 Honcho, Kawaguchi, Saitama 332-0012, Japan

Our research group aims to develop chemical assembly lines that concisely generate

natural products and their variants having different skeletal, stereochemical and functional group properties. In this forum, I will introduce two topics: (1) Biogenetically-inspired synthesis and skeletal diversification of indole alkaloids, (2) Design and de novo synthesis of anti-malarial 6-aza-artemisinins. These approaches could pave the way to rapid and cost-effective production of skeletally diverse, readily modifiable, and natural product-relevant molecules that have been inaccessible by other means.

References

1) Oguri, H.* Chem. Rec. 2016, 16, 652. 2) Mizoguchi, H.; Oikawa , H.; Oguri, H.* Nat. Chem. 2014, 6, 57. 3) Mizoguchi, H.; Watanabe, R.; Minami, S.; Oikawa, H.; Oguri, H.* Org. Biomol. Chem. 2015, 13,

5955. 4) Reddy, B. K.; Hiruma, T.; Mizoguchi, H.; Ochiai, K.; Suzuki, S.; Oikawa, H.; Ishiyama, A.; Hokari, R.; Iwatsuki, M.; Otoguro, K.; Ōmura, S.; Oguri, H. submitted.

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26 

7th CCS-CSJ Young Chemists Forum 2017 －Frontier in Organic Synthesis toward Middle Molecular Strategy－

■Date March 18th (Sat), 2017 9:00-17:10 ■Venue S2; Room J24, House B, Bldg. 4,

Hiyoshi Campus, Keio University Yokohama, Kanagawa, Japan

■Hosted by The Chemical Society of Japan (CSJ) Co-hosted by The Chinese Chemical Society (CCS)

Publication: March 2017

Publisher: The Chemical Society of Japan

1-5, Kanda-Surugadai, Chiyoda-ku Tokyo, 101-8307, Japan

Copyright: The Chemical Society of Japan

um盟国① Suzuki-Coupling of Ar-Cl substrates② Borylation of bulky Ar-Cl substrates③ Regioselective C-H borylation④ Caged phoshines allow catalysts to be stable in the air.⑤ Palladium is separated from the products by Celite刊tration. 1>

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pinB-Bpin 1.0 eq. KOAc3.0eq. toluene, 16 h

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Silica-SMAP 0.5 mol% Pd(0Ac)2 0.5 or 1.0 mol%

pinB-Bpin 1.0 eq. KOAc3.0eq.

benzene, 16 h

cト：手Entry Ligand [Pd］／山 NMRYield 例）

Silica-SMAP 1 :1 93 2 SPhos 1 :1 。

3 SPhos 1 :2 。

4 XPhos 1 :1 。

5 XPhos 1 :2 。

8 0℃，8 5% 90℃，89% 90℃，90% 1110℃，72% 110℃，83% Depending Silica-SMAP is a highly on the substrate, active than Buchwald Ligand .

Borylation of bulky Ar-Cl substrates

�亙亙1) Hamasaka, G., Ochida, K , Hara, K., and Sawamura, M.: Angew. Chem. Int. Ed., 46, 5381 (2007).

2) Kawamorita, S., Ohmiya, H., lwai, T. and Sawamura, M. :Angew. Chem. Int. Ed., 50, 8363 (2011).

3) Kawamorita, S., Ohmiya, H.,Hara, K., Fukuoka, A. and Sawamura, M. : J. Am. Chem. Soc., 14, 5058 (2009).

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Silica-SMAP Organic Synthesis 193-17453

Wako Pure Chemical Industries, Ltd.

Online Catalog: www.e-reagent.com USA: labchem@wakousa.com Eu rope: biochem@wako-chemicals.de Others: cservice@wako-chem.co.jp

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