Efforts towards the identification of simpler platensimycin analogues--the total synthesis of oxazinidinyl platensimycin.
Epimerization and stapling in one pot: A facile synthesis of an oxazinidinyl analogue of the antibiotic platensimycin is presented. Key steps of this work are a novel dynamic ring-closing metathesis (RCM) that involves a base-catalyzed epimerization followed by a tandem Ru-catalyzed metathesis, and a nucleophilic addition to a ketone followed by a subsequent intramolecular epoxide ring-opening reaction to construct the core structure of the target molecule (see scheme).
Wang
Jingxin
J
Department of Chemistry and Biochemistry, University of Maryland, College Park, MD 20742, USA.
Lee
Vincent
V
Sintim
Herman O
HO
D000218:Adamantane / Q000138:chemical synthesis* / Q000737:chemistry; D062365:Aminobenzoates / Q000138:chemical synthesis* / Q000737:chemistry; D000813:Anilides / Q000138:chemical synthesis* / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure
D062365:Aminobenzoates; D000813:Anilides; D000900:Anti-Bacterial Agents; D000218:Adamantane; C510909:platensimycin