Application of aryl siloxane cross-coupling to the synthesis of allocolchicinoids

WM Seganish, P DeShong

Index: Seganish, W. Michael; DeShong, Philip Organic Letters, 2006 , vol. 8, # 18 p. 3951 - 3954

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Citation Number: 60

Abstract

In this communication, we report a new approach to the allocolchicine carbocyclic skeleton based upon an aryl siloxane coupling reaction and a phenanthrol ring expansion. These key steps allow for the selective functionalization of every carbon within the carbocyclic framework. The siloxane coupling-phenanthrol sequence was applied to the synthesis of two allocolchicinoids, including the first fully synthetic approach to N-acetyl colchinol-O- ...