Sequential ring-closing metathesis-vinyl halide Heck cyclization reactions: access to the tetracyclic ring system of ervitsine

被引：21
|
作者：
Bennasar, M-Lluisa [1 ]
Zulaica, Ester
Sole, Daniel
Alonso, Sandra
机构：
[1] Univ Barcelona, Fac Pharm, Organ Chem Lab, E-08028 Barcelona, Spain
来源：
TETRAHEDRON | 2012年 / 68卷 / 24期
关键词：
Alkaloids; Ervitsine; Ring-closing metathesis; Heck cyclization; SYNTHETIC APPLICATIONS; INDOLE ALKALOIDS; STEREOCONTROLLED SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; STRYCHNOS ALKALOIDS; OLEFIN METATHESIS; CONCISE SYNTHESIS; PALLADIUM; INTERMEDIATE; HETEROCYCLES;
D O I：
10.1016/j.tet.2012.04.022
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A chemoselective indole-templated ring-closing metathesis is used to assemble the cyclohepta[b]indole substructure of the indole alkaloid ervitsine. A subsequent intramolecular Heck coupling of the resulting alkene functionality with an amino-tethered vinyl halide accomplishes the closure of the unique 2-azabicyclo[4.3.1]decane framework of the alkaloid with concomitant incorporation of the exocyclic E-ethylidene substituent. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4641 / 4648
页数：8
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