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Review | Regular issue | Vol 78, No. 7, 2009, pp.1667-1713
Published online, 25th February, 2009
DOI: 10.3987/REV-09-652
■ Recent Advances in the Syntheses of Biologically Active Natural Products Using Biocatalyst

Hiroyuki Akita*

*School of Pharmaceutical Sciences, Toho University, 2-2-1, Miyama, Funabashi, Chiba 274-8510, Japan

Abstract

This review summarizes the chemoenzymatic synthesis of biologically active natural products based on a combination of chemical diastereoselectivity and enzymatic enantioselectivity using lipase. Diastereoselective synthesis of (±)-(2,3)-syn-2-methyl-3-hydroxy ester I or (±)-(2,3)-syn-3-methyl-2-hydroxy ester III was achieved based on diastereoselective reduction of (±)-2-methyl-3-keto ester IV or the reaction of (±)-trans-epoxybutanoate V and carbon-nucleophile, respectively. These racemic alcohols were subjected to enzymatic resolution to afford the corresponding enantiomers. Each enantiomerically pure compound was converted to biologically active natural products such as oudemansins, chuangxinmycin, asperlin, indolmycin, cystothiazoles, melithiazols and myxothiazols possessing antifungal and cytotoxic activities, inhibition of NADH oxidation, etc.