Citation: Xiao Yin YANG, Christian HAUG, Yi Ping YANG, Zhi Sheng HE, Yang YE. Stereoselective Synthesis of syn-and anti-3a-Hydroxyl-1, 2, 3, 3a, 8, 8a-hexahydropyrrolo[2,3-b] indole-2-carboxylic Acid[J]. Chinese Chemical Letters, ;2003, 14(2): 130-132. shu

Stereoselective Synthesis of syn-and anti-3a-Hydroxyl-1, 2, 3, 3a, 8, 8a-hexahydropyrrolo[2,3-b] indole-2-carboxylic Acid

1.
State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Shanghai Institutes for Biological Sciences, Chinese Academy of Science, Shanghai 200031;
2.
Current address:Bicoll Biotechnology (Shanghai) Co.Ltd., 518A Bibo Road, Shanghai 201203

Received Date: 19 April 2002

Fund Project: We are grateful for financial supports from Bayer AGCompany and National Natural Science Foundation of China (Grant Number 30123005)CH thanks the DAAD lor a scholarship from its program "Biowisscnschaften".

The structure of syn- and anti-N^b-(p-toluenesulfonyl)-3a-hydroxyl-1, 2, 3, 3a, 8, 8a-hexahydro pyrrolo[2,3-b] indole-2-carboxylic t-butyl ester was stereoselectively synthesized by oxidative ring formation of N^b-(p-toluenesulfonyl)-L-tryptophan t-butyl ester in methylene chloride containing dimethyldioxirane (DMDO), the p-toluenesulfonyl group and t-butyl group can be easily removed by sodium naphthalenide and trifluoroacetic acid, respectively.
- Oxidative ring formation,
- stereoselective synthesis,
- sodium naphthalenide
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