TOTAL SYNTHESIS OF LISSOCLINOLIDE BY ACID-INDUCED LACTONIZATION OF AN (E)-alpha-BROMO-gamma,delta-EPDXY ACRYLATE DERIVATIVE

摘要

The stereoselective total synthesis of lissoclinolide, a naturally occurring antibiotic and cytotoxic butenolide, was achieved in 10 steps including a highly E-selective Still-Gennari-type olefination and an acid-induced lactonization of an (E)-alpha-bromo-gamma,delta-epoxy acrylate derivative. The key regioselective 5-exo lactonization could be regulated by using AcOH under kinetically controlled conditions.