An Asymmetric Approach towards (-)-Aphanorphine and Its Analogues

被引：33
|
作者：
Donets, Pavel A. [1 ]
Goeman, Jan L. [2 ]
Van der Eycken, Johan [2 ]
Robeyns, Koen
Van Meervelt, Luc
Van der Eycken, Erik V. [1 ]
机构：
[1] Katholieke Univ Leuven, Lab Organ & Microwave Assisted Chem LO MAC, Dept Chem, B-3001 Louvain, Belgium
[2] Univ Ghent, Lab Organ & Bioorgan Synth, Dept Chem, B-9000 Ghent, Belgium
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 2009卷 / 06期
关键词：
Alkaloids; Asymmetric catalysis; Heck reaction; Radical reactions; Cyclization; FORMAL SYNTHESIS; (+)-APHANORPHINE; PALLADACYCLES; CATALYSTS; EFFICIENT; ESTERS; ROUTE;
D O I：
10.1002/ejoc.200801175
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A short enantioselective approach towards the alkaloid (-)-aphanorphine and its substituted analogues is described. The enantiomerically pure starting material for the synthesis was obtained by asymmetric hydrogenation in the presence of the Rh-(S)-PipPhos complex. Microwave-assisted Heck cyclization selectively provided the seven-membered 3-benzazepine ring. Further, the assembly of the tricyclic core of the alkaloid was accomplished by intramolecular radical cyclization. The X-ray structure confirming the absolute configuration of the obtained products is described. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
引用
收藏
页码：793 / 796
页数：4
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