Synthesis of Acetomycin Bislactone Analogues

Abstract

Bislactones 5 and 6 have been designed as esterase-resistant acetomycin analogues and prepared in 10 steps from methyl 2-methylacetoacetate. Consecutive quaternary and tertiary carbon centers at the C-3 and C-4 positions on the γ-lactone ring are constructed by Pd-catalyzed allylic alkylation in one step. The relative stereochemistry for 6 has been determined by X-ray crystallographic analysis.

Key word

bioorganic chemistry - palladium - esterase - stereoselective synthesis - γ-lactone

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