3 years ago

Total Synthesis of (−)-Albocycline

Total Synthesis of (−)-Albocycline
Rodrigo B. Andrade, Vijay K. Chatare
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. An antibiotic candidate: A concise total synthesis of the macrolactone (−)-albocycline in 14 steps from methyl (R)-3-hydroxybutyrate is reported. Key steps are the highly regio- and stereoselective reactions of chiral N-sulfinyl metallodienamines with aldehydes and the Davis oxaziridine, in addition to the Horner–Wadsworth–Emmons olefination of N-sulfinyl imines.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201702530

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