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Total Synthesis of (−)‐Albocycline
Author(s) -
Chatare Vijay K.,
Andrade Rodrigo B.
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201702530
Subject(s) - total synthesis , natural product , stereoselectivity , oxaziridine , stereochemistry , chemistry , staphylococcus aureus , combinatorial chemistry , organic chemistry , biology , bacteria , catalysis , genetics
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.