THE CHEMISTRY OF CYCLIC TAUTOMERS OF TRYPTOPHAN - TOTAL SYNTHESIS OF (+)-(ENT)-PSEUDOPHRYNAMINOL

被引:21
作者
CRICH, D
PAVLOVIC, AB
SAMY, R
机构
[1] University of Illionis at Chicago, Department of Chemistry (M/C111), Chicago, IL 60607-7061
关键词
D O I
10.1016/0040-4020(95)00307-T
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A diastereoselective synthesis of the unnatural (+)-enantiomer of the hexahydropyrroloindole alkaloid (-)-pseudophrynaminol (3), isolated from the skin of the Australian frog Pseudophryne coriacea, from a cyclic tautomer (1) of L-tryptophan, is described, The CD spectrum of the synthetic 3 is opposite in sign to that of the natural material enabling the configuration of the natural product to be established as 3aS,8aR.
引用
收藏
页码:6379 / 6384
页数:6
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