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Paper | Special issue | Vol 79, No. 1, 2009, pp.721-738
Published online, 3rd December, 2008
DOI: 10.3987/COM-08-S(D)38
Stereocontrolled Total Synthesis of (±)-FR901483

Shigeru Ieda, Yusuke Asoh, Teppei Fujimoto, Haruka Kitaoka, Toshiyuki Kan, and Tohru Fukuyama*

*Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan

Abstract

The total synthesis of potent immunosuppressant FR901483 (1) is reported. The remarkable feature of our convergent synthesis is the p-methoxybenzyl and methylamino groups are stereoselectively incorporated within the tri-cyclic core skeleton. The skeleton itself is constructed by an intramolecular aldol reaction on a symmetrical keto-aldehyde (14), which is readily derived by an eight-step sequence from nitromethane and methyl acrylate.