A simple, short, and flexible synthesis of viridiofungin derivatives.
Described herein is a simple, flexible, and efficient synthesis of the skeleton of the viridiofungins, a family of microbial secondary metabolites. The synthesis utilizes an asymmetric aldol reaction of a chiral oxazolidinone, a diastereoselective alkylation of a chiral 1,3-dioxolan-2-one, and a geometrically selective alkene cross-metathesis reaction as the key C-C bond-forming steps.
Goldup
Stephen M
SM
Department of Chemistry, Imperial College London, Exhibition Road, London SW7 2AZ, England.
Pilkington
Christopher J
CJ
White
Andrew J P
AJ
Burton
Andrew
A
Barrett
Anthony G M
AG
D000478:Alkylation; D000596:Amino Acids / Q000737:chemistry*; D002384:Catalysis; D002951:Citrates / Q000138:chemical synthesis / Q000737:chemistry*; D004952:Esters / Q000737:chemistry; D008293:Malates / Q000737:chemistry; D015394:Molecular Structure
D000596:Amino Acids; D002951:Citrates; D004952:Esters; D008293:Malates; C030298:malic acid