Alkyne Carbonyl Metathesis As a Means To Make 4-Acyl Chromenes: Syntheses of (±)-Deguelin and (±)-Munduserone

Abstract

A highly convergent synthetic approach to rotenoid natural products is described. Successful pairing of two building blocks for Sonogashira cross-coupling and intramolecular alkyne carbonyl metathesis allows ready access to 4-acylchromene, a key substructure of these natural products, leading to syntheses of (±)-deguelin and (±)-munduserone in high overall yields.