Oxidative Cleavage in the Construction of Complex Molecules: Synthesis of the Leucascandrolide A Macrolactone

Abstract

Oxidation leads to macrolactone: Oxidative carbon–carbon bond activation is a key step in the formal synthesis of leucascandrolide A, which is formed in one step from 1. Additional features are stereoselective BiBr3-mediated allylation, acetal formation as a fragment-coupling reaction, and a rhenium-mediated allylic alcohol transposition leading to stable macrolactol formation.