Tetrahedron

A three-carbon (n+ 1+ 2) ring expansion method for the synthesis of macrocyclic enones. Application to muscone synthesis

I Erden, W Cao, M Price, M Colton

Index: Erden, Ihsan; Cao, Weiguo; Price, Mary; Colton, Michael Tetrahedron, 2008 , vol. 64, # 23 p. 5497 - 5501

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Citation Number: 6

Abstract

The three-carbon ring expansion methodology commences with the preparation of a cyclic allene (C9, C11, C13), readily available from the corresponding cycloalkene via dibromocarbene addition and subsequent treatment with methyllithium. Dichloroketene addition to the cyclic allene regioselectively provides the [2+ 2] cycloadduct, which is reductively dechlorinated with zinc in methanol. The resulting cyclobutanone is then ...