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. 2013 Jan 18;78(2):455-65.
doi: 10.1021/jo302362b. Epub 2012 Dec 18.

Enantioselective total syntheses of (-)-FR901483 and (+)-8-epi-FR901483

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Enantioselective total syntheses of (-)-FR901483 and (+)-8-epi-FR901483

Hao-Hua Huo et al. J Org Chem. .

Abstract

The enantioselective total syntheses of the potent immunosuppressant FR901483 (1) and its 8-epimer (47) have been accomplished. Our approach features the use of building block 6 as the chiron, the application of the one-pot amide reductive bis-alkylation method to construct the chiral aza-quaternary center (dr = 9:1), regio- and diastereoselective intramolecular aldol reaction to build the bridged ring, and RCM to form the 3-pyrrolin-2-one ring.

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