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
posted on 2002-11-27, 00:00authored byTimothy 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.