Enantioselective synthesis of cadinanes starting from R-(-)-or S-(+)-carvone

被引:10
作者
Baranovsky, AV
Jansen, BJM
Meulemans, TM
de Groot, A
机构
[1] Agr Univ Wageningen, Organ Chem Lab, NL-6703 HB Wageningen, Netherlands
[2] Byelarussian Acad Sci, Inst Bioorgan Chem, Lab Steroid Chem, Minsk 220141, BELARUS
关键词
D O I
10.1016/S0040-4020(98)00234-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new enantioselective synthesis of cadinanes, using the Mukaiyama-Michael reaction, was developed starting from R-(-)- or S-(+)-carvone. This approach gives an easy and direct access to the cadinane skeleton and the scope proved to be complementary to a formylation-annelation sequence. The applicability of the method was demonstrated by the enantioselective synthesis of 1,9-cadinadien-3-one and 4-methoxy-1,9-cadinadien-3-one. (C) 1998 Elsevier Science Ltd. All rights reserved.
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页码:5623 / 5634
页数:12
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