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Enantioselective synthesis of marine indole alkaloid hamacanthin B
Biao Jiang1, Cai-Guang Yang, Jun Wang
1The State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, Peoples Republic of China. jiangb@pub.sioc.ac.cn
The Journal of Organic Chemistry
|February 16, 2002
Abstract:
An enantioselective total synthesis of hamacanthin B (1) is described. This synthesis is based on the asymmetric synthesis of (S)-2-azido-(indol-3-yl)ethylamine 7, which is coupled with the 3-indolyl-alpha-oxoacetyl chloride 8 and subsequently used in a successful intramolecular Staudinger-aza Wittig cyclization to form the central dihydropyrazinone ring. The stereochemistry of naturally isolated hamacanthin B is revealed as the (S)-configuration.