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

Aya Fujino, Takeshi Sugai

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

(R)-3-Hydroxy-3-methyl-5-hexanoic acid p-methoxybenzyl ester 1b was prepared by carbonchain 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.

Original languageEnglish
Pages (from-to)1712-1716
Number of pages5
JournalAdvanced Synthesis and Catalysis
Volume350
Issue number11-12
DOIs
Publication statusPublished - 2008 Aug 4

Keywords

  • Amidase
  • Bioconversion
  • Epoxide hydrolase
  • Hydrolysis
  • Kinetic resolution
  • Nitrile hydratase

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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