Bacillus subtilis epoxide hydrolase-catalyzed preparation of enantiopure 2-methylpropane-1,2,3-triol monobenzyl ether and its application to expeditious synthesis of (R)-bicalutamide

Aya Fujino, Masayoshi Asano, Hitomi Yamaguchi, Naoki Shirasaka, Akiko Sakoda, Masaya Ikunaka, Rika Obata, Shigeru Nishiyama, Takeshi Sugai

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27 Citations (Scopus)

Abstract

Expeditious synthesis of (R)-bicalutamide (1), a synthetic antiandrogen, from enantiopure 2-methylpropane-1,2,3-triol monobenzyl ether (4) was achieved. An engineered Bacillus subtilis epoxide hydrolase worked enantioselectively on the racemic epoxide (7) to provide the above starting material in highly enantiomerically enriched state.

Original languageEnglish
Pages (from-to)979-983
Number of pages5
JournalTetrahedron Letters
Volume48
Issue number6
DOIs
Publication statusPublished - 2007 Feb 5

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Keywords

  • (R)-1-Benzyloxy-2-methylpropane-2,3-diol
  • Bicalutamide
  • Diol
  • Epoxide hydrolase
  • Kinetic resolution

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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