Reversal of the Diastereoselectivity in a Sequence of Cycloaddition Reactions: [2+2+2], Ene Type, [4+2]. A Totally Stereoselective Access to the Basic Skeleton of the Kaurane Family.

Paul Cruciani; Corinne Aubert; Max Malacria

doi:10.1055/s-1996-5315

Synlett 1996; 1996(1): 105-107
DOI: 10.1055/s-1996-5315

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Reversal of the Diastereoselectivity in a Sequence of Cycloaddition Reactions: [2+2+2], Ene Type, [4+2]. A Totally Stereoselective Access to the Basic Skeleton of the Kaurane Family.

Paul Cruciani, Corinne Aubert, Max Malacria^*

^*Université Pierre et Marie Curie, Paris VI. Laboratoire de Chimie Organique de Synthèse, associé au CNRS, tour 44-54, B. 229, 4, Place Jussieu 75252 - Paris Cedex 05, France

Abstract

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A dramatic synergic influence of substituents present in the allylic endocyclic position of the methylenecyclopentane unit and of a carbonyl group on the tether enabled, for the first time, a totally stereoselective access to the basic skeleton of the kaurane family via a sequence of cyclizations: a [2+2+2] cyclotrimerization, an ene type reactions and an intramolecular [4+2] reaction.

ene type reaction - [2+2+2] cycloaddition - cobalt(I) - [4+2] cyclization - diastereoselectivity

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