Synthesis of enantiopure cis-decahydroquinolines from homotyramines by Birch reduction and aminocyclization

被引：5

作者：

Mena, Marisa ^{[1
]}

Valls, Nativitat ^{[1
]}

Borregan, Mar ^{[1
]}

Bonjoch, Josep ^{[1
]}

机构：

[1] Univ Barcelona, Fac Farm, Lab Quim Organ, E-08028 Barcelona, Spain

来源：

TETRAHEDRON | 2006年 / 62卷 / 39期

关键词：

lepadin alkaloids; decahydroquinolines; epoxides; conformational analysis; nitrogen heterocycles;

D O I：

10.1016/j.tet.2006.07.035

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Birch reduction of homotyramines with a syn-beta-amino alcohol unit followed by acid treatment of formed dihydroanisole derivatives gives polysubstituted enantiopure cis-decahydroquinolines. The stereoselectivity of the process differs if the hydroxyl group is free or protected. The procedure allows the synthesis of 7-oxodecahydroquinolines embodying four stereogenic centres with the same relative configuration as that of lepadins F and G. (c) 2006 Elsevier Ltd. All rights reserved.

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页码：9166 / 9173

页数：8

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