Total Synthesis of (-)-Albocycline
Vijay K Chatare1, Rodrigo B Andrade1
1Department of Chemistry, Temple University, 1901 N. 13thSt., Philadelphia, PA, 19122, USA.
Abstract:
The macrolactone natural product (-)-albocycline is a promising antibiotic candidate for the treatment of both methicillin resistant Staphylococcus aureus (MRSA) and vancomycin-resistant strains. Herein we report a concise total synthesis of (-)-albocycline 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.
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