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Title:
METHOD FOR ASYMMETRICALLY SYNTHESIZING ASPIDOSPERMA ALKALOID
Document Type and Number:
WIPO Patent Application WO/2018/099146
Kind Code:
A1
Abstract:
Disclosed is a method for asymmetrically synthesizing aspidosperma alkaloid. In this method, a key intermediate of formula (4) is obtained by 6 steps of reactions, including [4+2] cycloaddition of the compound of formula (1a) and the compound of formula (1b), decarboxylation, reduction, Wittig reaction, oxidation and Fischer indole rearrangement, and further transformed through several steps to obtain a series of aspidosperma alkaloids. The reaction scheme is shown in scheme (1). The method can start from abundant and readily available compounds of formulas (1a) and (1b), and provides good technical support for subsequent realization of large-scale production of the aspidosperma alkaloid and study of structure-activity relationship.

Inventors:
JIANG, Xuefeng (No.3663, North Zhongshan Road Putuo District, Shanghai 2, 200062, CN)
WANG, Nengzhong (No.3663, North Zhongshan Road Putuo District, Shanghai 2, 200062, CN)
BAI, Leiyang (No.3663, North Zhongshan Road Putuo District, Shanghai 2, 200062, CN)
Application Number:
CN2017/098979
Publication Date:
June 07, 2018
Filing Date:
August 25, 2017
Export Citation:
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Assignee:
EAST CHINA NORMAL UNIVERSITY (No.3663, North Zhongshan Road Putuo District, Shanghai 2, 200062, CN)
International Classes:
C07D471/20; C07B53/00; C07D209/08; C07D487/10
Foreign References:
US3987048A1976-10-19
Other References:
WANG, NENGZHONG ET AL.: "Divergent Asymmetric Total Synthesis of (+)-Vincadifformine, (-)-Quebrachamine, (+)-Aspidospermidine, (-)-Aspidospermine, (-)-Pyrifolidine, and Related Natural Products", ORGANIC LETTERS, vol. 19, no. 12, 1 June 2017 (2017-06-01), pages 3167 - 3170, XP055490472
GIRI, V.S. ET AL.: "Convenient Total Synthesis of (dl)-quebrachamine", J. HETROCYCLIC CHEM., vol. 17, 31 July 1980 (1980-07-31), pages 1133 - 1134
MANDAL, S.B. ET AL.: "Reduction of Lactams and Thiolactams by Sodium Borohydride: Application in the Synthesis of Some Alkaloids", J. ORG. CHEM., vol. 53, no. 18, 31 December 1988 (1988-12-31), pages 4236 - 4241, XP002108421
Attorney, Agent or Firm:
MSJ LAW OFFICE (Maggie Dong, Room 301BBuilding 358, No.3663, North Zhongshan Road, Putuo District, Shanghai 2, 200062, CN)
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