De novo formal synthesis of (-)-virginiamycin M2 via the asymmetric hydration of dienoates.
A de novo approach to the formal total synthesis of the macrolide natural product (-)-virginiamycin M2 has been achieved via a convergent approach. The absolute and relative stereochemistry of the nonpeptide portion of (-)-virginiamycin M2 was introduced by two Sharpless asymmetric dihydroxylation reactions.
Mortensen
Matthew S
MS
Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506, USA.
Osbourn
Joshua M
JM
O'Doherty
George A
GA
D002384:Catalysis; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism; D014769:Virginiamycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry
D018942:Macrolides; C522302:virginiamycin M2; D014769:Virginiamycin