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Paper | Special issue | Vol 59, No. 1, 2003, pp.169-187
Published online, 1st January, 1970
DOI: 10.3987/COM-02-S11
A Formal Total Synthesis of Securinine via an Intramolecular [4+2]Cycloaddition Reaction

Toshio Honda,* Hidenori Namiki, Mika Kudoh, Hiromasa Nagase, and Hirotake Mizutani

*Faculty of Pharmaceutical Sciences, Hoshi University, 2-4-41 Ebara, Shinagawa-ku, Tokyo 142-8501, Japan

Abstract

An intramolecular Diels-Alder reaction of the enol ester derived from 2-acetylpyridine and sorbic anhydride gave the cycloaddition product, stereoselectively, which was further converted into the key intermediate for the synthesis of securinine.