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Paper | Special issue | Vol 86, No. 2, 2012, pp.1071-1092
Published online, 28th August, 2012
DOI: 10.3987/COM-12-S(N)38
STEREOCONTROLLED TOTAL SYNTHESIS OF (−)-FR901483

Shigeru Ieda, Akitaka Masuda, Mami Kariyama, Toshiyuki Wakimoto, Tomohiro Asakawa, Tohru Fukuyama,* and Toshiyuki Kan*

*Synthetic Organic & Medicinal Chemistry, School of Pharmaceutical Science, University of Shizuoka, 52-1 Yada, Suruga, Shizuoka 422-8526, Japan

Abstract

The total synthesis of a potent immunosuppressant (–)-FR901483 is accomplished. The skeleton itself is constructed by the Ugi 4CC reaction, subsequent intramolecular Dieckmann condensation, and a diastereoselective intramolecular aldol reaction. However, the remarkable feature is the stereoselective incorporation of the p-methoxybenzyl and methylamino groups within the tricyclic core skeleton.