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Full Paper
Chemoenzymatic Approach to Enantiomerically Pure (R)-3-Hydroxy-3-methyl-4-pentenoic Acid Ester and Its Application to a Formal Total Synthesis of Taurospongin A
Article first published online: 9 JUL 2008
DOI: 10.1002/adsc.200800191
Copyright © 2008 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Fujino, A. and Sugai, T. (2008), Chemoenzymatic Approach to Enantiomerically Pure (R)-3-Hydroxy-3-methyl-4-pentenoic Acid Ester and Its Application to a Formal Total Synthesis of Taurospongin A. Adv. Synth. Catal., 350: 1712–1716. doi: 10.1002/adsc.200800191
Publication History
- Issue published online: 31 JUL 2008
- Article first published online: 9 JUL 2008
- Manuscript Received: 30 MAR 2008
Funded by
- Grant-in-Aid for Scientific Research. Grant Number: 18580106
- “High-Tech Research Center” Project for Private Universities
- Ministry of Education, Culture, Sports, Science and Technology, Japan
Keywords:
- amidase;
- bioconversion;
- epoxide hydrolase;
- hydrolysis;
- kinetic resolution;
- nitrile hydratase
Abstract
(R)-3-Hydroxy-3-methyl-5-hexanoic acid p-methoxybenzyl ester 1b was prepared by carbon-chain elongation on both termini of the starting material, (R)-3-benzyloxy-2-methylpropane-1,2-diol 2a, which was prepared by an over-expressed Bacillus subtilis epoxide hydrolase-catalyzed enantioselective hydrolysis of the racemic 1-benzyloxymethyl-1-methyloxirane 3. One of the key steps of the requisite transformation was the Rhodococcus rhodochrous NBRC 15564-mediated hydrolysis of a cyano group to a carboxyl group under neutral conditions, to exclude any racemization of the intermediate and/or product. The enantiomerically pure form of (R)-1b was applied to a new formal total synthesis of taurospongin A.