American Chemical Society
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First Comprehensive Bakkane Approach:  Stereoselective and Efficient Dichloroketene-Based Total Syntheses of (±)- and (−)-9-Acetoxyfukinanolide, (±)- and (+)-Bakkenolide A, (−)-Bakkenolides III, B, C, H, L, V, and X, (±)- and (−)-Homogynolide A, (±)-Homogynolide B, and (±)-Palmosalide C

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journal contribution
posted on 2002-11-27, 00:00 authored by Timothy J. Brocksom, Fernando Coelho, Jean-Pierre Deprés, Andrew E. Greene, Marco E. Freire de Lima, Olivier Hamelin, Benoît Hartmann, Alice M. Kanazawa, Yanyun Wang
Cycloaddition of dichloroketene with dimethylcyclohexenes has been used as the key reaction in an efficient, general approach to the bakkanes. New methods and methodologies that have been developed in this work include spiro β-methylene-γ-butyrolactonizations, a vicinal dicarboxylation, an angelic ester preparation, a transesterification, an epoxy ketone double reduction, and a retro aldol−aldol approach to low-energy aldol isomers.