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Chatare VK , Andrade RB
Total Synthesis of (-)-Albocycline
Angew Chem Int Ed Engl. 2017 May 15;56(21) :5909-5911
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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.
1521-3773 Chatare, Vijay K Andrade, Rodrigo B Orcid: 0000-0002-4554-8323 Journal Article Research Support, Non-U.S. Gov't Research Support, U.S. Gov't, Non-P.H.S. Germany Angew Chem Int Ed Engl. 2017 May 15;56(21):5909-5911. doi: 10.1002/anie.201702530. Epub 2017 Apr 21.