Tetrahedron

Mild and rapid method for the generation of o-quinone methide intermediates. Synthesis of puupehedione analogues

…, MM Herrador, P Arteaga, M Cortés, J Benites…

Index: Barrero, Alejandro F.; Quilez del Moral, Jose F.; Mar Herrador; Arteaga, Pilar; Cortes, Manuel; Benites, Julio; Rosellon, Antonio Tetrahedron, 2006 , vol. 62, # 25 p. 6012 - 6017

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Citation Number: 31

Abstract

A route to simpler analogues to bioactive puupehedione derivatives involving a hetero Diels– Alder cycloaddition of a o-quinone methide is described. These intermediate species are generated via fluoride-induced desilylation of silyl derivatives of o-hydroxybenzyl iodides. Remarkable short reaction times and very mild experimental conditions are the main features of this method.