Tetrahedron

An oxidative coupling for the synthesis of arylated quaternary stereocentres and its application in the total synthesis of powelline and buphanidrine

KM Bogle, DJ Hirst, DJ Dixon

Index: Bogle, Katherine M.; Hirst, David J.; Dixon, Darren J. Tetrahedron, 2010 , vol. 66, # 33 p. 6399 - 6410

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Citation Number: 13

Abstract

Catechol derivatives directly bonded to all-carbon quaternary stereocentres are prevalent in nature. An oxidative coupling strategy for the synthesis of this motif is described. Pivoting on the base-catalysed Michael addition of carbon-centred pro-nucleophiles to in situ generated ortho-benzoquinones, the method is broad in scope, high yielding and provides remarkably simple access to this challenging motif. The application of this methodology in the total ...