amphidinolide-e and dictyostatin

Key dienoic or dienal substructures of cytotoxic macrolides amphidinolide E and dictyostatin have been prepared via a Michael addition (followed by elimination of X-) of chiral enolates on beta-halo derivatives of ethyl acrylate, with full retention of the initial E or Z configuration. Evans oxazolidin-2-ones and our related thiazolidin-2-ones, as well as a fine-tuning of the reaction conditions, have been essential. Many chiral building blocks are accessible from these adducts.

Topics: Bridged Bicyclo Compounds, Heterocyclic; Catalysis; Macrolides; Molecular Structure; Propane; Stereoisomerism