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Paper | Special issue | Vol 97, No. 2, 2018, pp.1019-1027
Published online, 12th April, 2018
DOI: 10.3987/COM-18-S(T)84
Total Synthesis of Lissoclinolide by Acid-Induced Lactonization of an (E)-α-Bromo-γ,δ-Epoxy Acrylate Derivative

Kenichi Kobayashi,* Keisuke Kuwahara, Kosaku Tanaka III, Risako Kunimura, and Hiroshi Kogen*

*Graduate School of Pharmaceutical Sciences, Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan


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)-α-bromo-γ,δ-epoxy acrylate derivative. The key regioselective 5-exo lactonization could be regulated by using AcOH under kinetically controlled conditions.