A general asymmetric route for the synthesis of the alexine and australine family of pyrrolizidine alkaloids.: The first asymmetric synthesis of 1,2-diepi-alexine and 1,2,7-triepi-australine

被引：22

作者：

Chikkanna, D ^{[1
]}

Singh, OV ^{[1
]}

Kong, SB ^{[1
]}

Han, H ^{[1
]}

机构：

[1] Univ Texas, Dept Chem, San Antonio, TX 78249 USA

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 51期

基金：

美国国家卫生研究院;

关键词：

pyrrolizidine alkaloids; regioselective asymmetric aminohydroxylation; olefin cross metathesis; epoxidation; double cyclization;

D O I：

10.1016/j.tetlet.2005.10.074

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first asymmetric synthesis of 1,2-diepi-alexine and 1,2,7-triepi-australine (both are unknown at present) is described, which utilized the regioselective asymmetric aminohydroxylation (RAA) reaction of the achiral olefin VI, the cross metathesis (CM) reaction of the terminal olefin 8, and the formation and subsequent intramolecular double cyclization (DC) reactions of the epoxides 10 and 11. The C1 stereocenter was diastereoselectively introduced by the reaction of the aldehyde 7 with vinylmagnesium bromide. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：8865 / 8868

页数：4

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