The macrolactone natural product (–)-albocycline is a promising antibiotic candidate for the treatment of both methicillin resistant Staphylococcus aureus (MRSA) and vancomycin-resistant strains. A concise total synthesis of (–)-albocycline has been accomplished in 14 steps from commercially available methyl (R)-3-hydroxybutyrate. Novel key steps include the highly regio- and stereoselective reactions of chiral N-sulfinyl metallodienamines (NSMDs) with aldehydes and the Davis oxaziridine, in addition to the Horner-Wadsworth-Emmons olefination of N-sulfinyl imines.

N-sulfinyl metallodienamines in the total synthesis of (–)-albocycline

254th National Meeting (2017)

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