Studies on the Synthesis of Highly Oxidized Complex Natural Products of Biological Significance

2015 Fiscal Year Final Research Report

• Project/Area Number: 23000006
• Research Category: Grant-in-Aid for Specially Promoted Research
• Allocation Type: Single-year Grants
• Review Section: Science and Engineering; Chemistry
• Research Institution: Tokyo Institute of Technology
• Principal Investigator: SUZUKI Keisuke 東京工業大学, 大学院理工学研究科, 教授 (90162940)
• Co-Investigator(Kenkyū-buntansha): OHMORI Ken 東京工業大学, 大学院理工学研究科, 准教授 (50282819) ; ANDO Yoshio 東京工業大学, 大学院理工学研究科, 助教 (40532742) ; TAKIKAWA Hiroshi 東京工業大学, 大学院理工学研究科, 助教 (70550755) ; TAKAHASHI Haruko 東京工業大学, 男女共同参画推進センター, 助教 (40297601) ; MATSUMOTO Takashi 東京薬科大学, 薬学部, 教授 (70212222) ; KUSUMI Takenori 東京工業大学, 大学院理工学研究科, 特任教授 (70015882)
• Project Period (FY): 2011 – 2015
• Keywords: 酸化 / 多環芳香族 / ポリケチド / ポリフェノール / 複合糖質

Outline of Final Research Achievements

The project has dealt with the total synthesis of highly oxidized complex natural products, including (1) polyketides, (2) polyphenols, and (3) glycoconjugates with polycyclic structures. Subject 1 exploited isoxazole as a platform for stereo-controlled dimerization of anthraquinone and installation of angular cis-diol, enabling total syntheses of BE-43472B, pleospdione, and tetracenomycin C. Study on the pyranonaphthoquinone dimers led to the development of unusual dimerization protocols, enabling the first total synthesis of actinorhodin and a promising access to naphthocylines via thiolate-mediated dimerization protocol. Subject 2 was associated with synthesis of the catechin oligomers. Based on the concept of catechin–sugar analogy as well as the orthogonal activation, effective approaches have been established for synthesizing the linear as well as doubly-connected oligomers. Subject 3 dealt with the synthesis of bis-aryl C-glycoside antibiotics, and the first total synthesis of saptomycin B has been accomplished, enabling assignment of the C14-stereochmistry.

Free Research Field

化学