Total synthesis of marine natural products separacenes A and B

Abstract

A short and convergent route for the stereoselective total synthesis of separacenes A and B has been developed using (+)-methyl D-lactate and D-(−)-tartaric acid as the chiral pools. The characteristic features of this synthesis include the Trost–Rychnovsky alkyne rearrangement to construct the C₇–C₉ conjugated diene, the Horner–Wadsworth–Emmons olefination to form the C₅–C₆ and C₁₁–C₁₂ olefins and the Corey–Bakshi–Shibata reaction to install the C-13 hydroxy functionality.