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

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• 作者：M.-Lluï ; sa Bennasar ; ^{bennasar@ub.edu} ; Ester Zulaica ; Daniel Solé ; Sandra Alonso
• 关键词：Alkaloids ; Ervitsine ; Ring-closing metathesis ; Heck cyclization
• 刊名：Tetrahedron
• 出版年：2012
• 期刊代码：107_00404020
• 类别：ch
• 出版时间：17 June, 2012
• 卷：68
• 期：24
• 页码：4641-4648
• 文件大小：456 K

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.