STUDIES ON THE SYNTHESIS OF STRYCHNOS INDOLE ALKALOIDS

被引:13
作者
BOSCH, J
SALAS, M
AMAT, M
ALVAREZ, M
MORGO, I
ADROVER, B
机构
[1] Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona
关键词
INDOLE; STRYCHNOS ALKALOIDS; NUCLEOPHILIC ADDITION TO PYRIDINIUM SALTS;
D O I
10.1016/S0040-4020(01)87138-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Tetracycles 3b-d, having the ABCD ring substructure of Strychnos alkaloids and a N(b)-(formylmethyl) substituent protected as an oxime or hydrazone derivative, have been prepared by nucleophilic addition of the enolate of indoleacetic ester 1 to pyridinium salts 2b-d followed by acid cyclization. The same one-pot, two-step sequence allowed the preparation of tetracycle 3f, which incorporates an alpha-methoxyacrylate chain at the piperidine beta-position.
引用
收藏
页码:5269 / 5276
页数:8
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