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Enantioselective Total Synthesis of Lycoposerramine-Z Using Chiral Phosphoric Acid Catalyzed Intramolecular Michael Addition

Author:
Zhang, Lan-De, Zhong, Lin-Rui, Xi, Jie, Yang, Xiao-Liang, Yao, Zhu-Jun
Source:
Journal of organic chemistry 2016 v.81 no.5 pp. 1899-1904
ISSN:
1520-6904
Subject:
Grignard reagents, chemoselectivity, cyclohexanones, enantioselectivity, organic chemistry, phosphoric acid
Abstract:
A new enantioselective total synthesis of phlegmarine-type Lycopodium alkaloid lycoposerramine-Z (1) has been accomplished, using one-pot chemoselective sequential additions of two different Grignard reagents to the bis-Weinreb-amide intermediate and an efficient construction of the fully fuctionalized cyclohexanone intermediate with a chiral phosphoric acid catalyzed enantioselective intramolecular Michael addition.
Agid:
5505993