Ring-opening aminolysis of sesquiterpene lactones: An easy entry to bioactive sesquiterpene derivatives. Synthesis of (+)-beta-cyperone and (-)-eudesma-3,5-diene from santonin.

被引:18
作者
Blay, G [1 ]
Cardona, L [1 ]
Garcia, B [1 ]
Garcia, CL [1 ]
Pedro, JR [1 ]
机构
[1] UNIV VALENCIA,FAC QUIM,DEPT QUIM ORGAN,E-46100 BURJASSOT,VALENCIA,SPAIN
关键词
D O I
10.1016/0040-4020(96)00571-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Santonin (1) and other sesquiterpene lactones (2-3) react with pyrrolidine and other cyclic secondary amines to afford gamma-hydroxyamides, which by elimination with mesyl chloride in pyridine-benzene at 80 degrees C give unsaturated amides 4a-4c, 5a-5c and 6. Starting from amides 5a-5c a series of bioactive compounds against Locusta migratoria have been prepared, differing in the oxidation states of the C-3 and C-12 carbon atoms. Starting from amides 5a and 6 two conjugated diene eudesmanes (+)-beta-cyperone (15) and (-)eudesma-3,5-diene (19) have been prepared involving an elaboration of the amide group of the side chain of the eudesmane skeleton. Copyright (C) 1996 Elsevier Science Ltd
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收藏
页码:10507 / 10518
页数:12
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