Synthesis of enantiopure (2R,3aS,7aS)-2-ethyloctahydroindol-6-one and its Fischer indolization

被引:16
作者
Bonjoch, J
Catena, J
Terricabras, D
Fernandez, JC
LopezCanet, M
Valls, N
机构
[1] Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona
关键词
D O I
10.1016/S0957-4166(97)00379-0
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A diastereoselective synthesis of (-)-2-ethyloctahydroindol-6-one 12 starting from O-methyl-L-tyrosine 1 is described. The process first involves the synthesis of enantiopure (-)-1-(4-methoxyphenyl)-2-butylamine 8, which, after Birch reduction, N-benzylation and acid treatment, renders the cis-fused azabicyclo 12. Studies on the Fischer indolization of 12 are also reported. (C) 1997 Elsevier Science Ltd.
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页码:3143 / 3151
页数:9
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