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

10 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

Fingerprint

Hydrolysis
Esters
Epoxide Hydrolases
Hydrolases
Acids
Bacilli
Elongation
4-pentenoic acid
taurospongin A
propylene oxide
3-hydroxyisoheptanoic acid

Keywords

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

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

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title = "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",
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.",
keywords = "Amidase, Bioconversion, Epoxide hydrolase, Hydrolysis, Kinetic resolution, Nitrile hydratase",
author = "Aya Fujino and Takeshi Sugai",
year = "2008",
month = "8",
day = "4",
doi = "10.1002/adsc.200800191",
language = "English",
volume = "350",
pages = "1712--1716",
journal = "Advanced Synthesis and Catalysis",
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publisher = "Wiley-VCH Verlag",
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TY - JOUR

T1 - 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

AU - Fujino, Aya

AU - Sugai, Takeshi

PY - 2008/8/4

Y1 - 2008/8/4

N2 - (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.

AB - (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.

KW - Amidase

KW - Bioconversion

KW - Epoxide hydrolase

KW - Hydrolysis

KW - Kinetic resolution

KW - Nitrile hydratase

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U2 - 10.1002/adsc.200800191

DO - 10.1002/adsc.200800191

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EP - 1716

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

SN - 1615-4150

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