Tandem Double Michael Addition/Sigmatropic Rearrangements for the Construction of Highly Substituted Rings: A Synthesis of the Taxol A Ring

Philip J. Parsons; Marijan Stefinovic

doi:10.1055/s-1993-22657

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Synlett 1993; 1993(12): 931-932
DOI: 10.1055/s-1993-22657

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Tandem Double Michael Addition/Sigmatropic Rearrangements for the Construction of Highly Substituted Rings: A Synthesis of the Taxol A Ring

Philip J. Parsons^* , Marijan Stefinovic

^*Department of Chemistry, University of Reading, Whiteknights, Reading RG6 2AD, Berkshire, England

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Publikationsdatum:
19. März 2002 (online)

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A new ring synthesis is described which relies on a double Michael addition of enolates derived from α,β-unsaturated ketones to allenyl sulphoxides. The resulting allylic sulphoxides can be isolated or rearranged in situ to cyclic allylic alcohols.