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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
Authors:Brocksom Timothy J  Coelho Fernando  Deprés Jean-Pierre  Greene Andrew E  Freire De Lima Marco E  Hamelin Olivier  Hartmann Benoît  Kanazawa Alice M  Wang Yanyun
Institution:Chimie Recherche (LEDSS), Université Joseph Fourier, BP 53X, 38041 Grenoble, France.
Abstract: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 beta-methylene-gamma-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.
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