A concise synthesis of (-)-mesembrine

被引：36

作者：

Dalko, PI ^{[1
]}

Brun, V ^{[1
]}

Langlois, Y ^{[1
]}

机构：

[1] Univ Paris Sud, CNRS, Lab Synth Subst Nat, ICMO, F-91405 Orsay, France

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 49期

关键词：

alkylation; sercocontrol; imidazoline; alkaloid;

D O I：

10.1016/S0040-4039(98)02032-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(-)-Mesembrine 11 was synthesized in 7 steps, in 19.4% overall yield and with ee>95%. The key step of the sequence is a stereoselective alkylation reaction of dianion derived from C-2 symmetric imidazolines allowing efficient formation of quaternary benzylic center. Chiral auxiliaries derived from (S,S)- 1,2-diaminocyclohexane la and (S,S)-1,2-diaminocyclohexane Ib were compared. This synthesis provided unambiguous correlation of the newly formed stereocenter. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

引用

页码：8979 / 8982

页数：4

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