Concise total synthesis of (+)-brefeldin A: a combined beta-lactone/cross-metathesis-based strategy.
[reaction: see text] A highly convergent total synthesis of (+)-brefeldin A that relies on a diastereoselective, beta-lactone-based cyclopentane synthesis combined with complex cross-metathesis reactions is described. The utility of beta-lactones for natural product synthesis and the versatility of cross-metathesis in this context were demonstrated, including the tolerance of an epimerizable aldehyde and a beta-lactone.
Wang
Yingcai
Y
Department of Chemistry, Texas A&M University, P.O. Box 30012, College Station 77842-3012, USA.
Romo
Daniel
D
D020126:Brefeldin A / Q000138:chemical synthesis* / Q000737:chemistry; D003432:Cross-Linking Reagents; D005658:Fungi / Q000737:chemistry; D007783:Lactones / Q000737:chemistry*; D015394:Molecular Structure
D003432:Cross-Linking Reagents; D007783:Lactones; D020126:Brefeldin A