A chemo-enzymatic expeditious route to racemic dihexanoyl (2R*,3R*,4R*)-dehydroxymethylepoxyquinomycin (DHMEQ), the precursor for lipase-catalyzed synthesis of the potent nuclear factor-κB inhibitor, (2 S,3S,4 S )-DHMEQ

Ryohei Kobayashi, Kengo Hanaya, Mitsuru Shoji, Kazuo Umezawa, Takeshi Sugai

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

In order to synthesize the potent nuclear factor (NF)- κB inhibitor, (2S ,3 S ,4 S )-dehydroxymethylepoxyquinomycin (DHMEQ), in a large scale, a new route for its corresponding racemic precursor, dihexanoyl (2R*,3R*, 4R*)- DHMEQ, was developed. By employing both hydroquinone and benzoquinone intermediates, the total yield, reproducibility, and synthetic steps were improved and the synthetic cost was reduced.

Original languageEnglish
Pages (from-to)1220-1223
Number of pages4
JournalChemical and Pharmaceutical Bulletin
Volume60
Issue number9
DOIs
Publication statusPublished - 2012 Sep 1

Keywords

  • Benzoquinone
  • Dehydroxymethylepoxyquinomycin
  • Epoxidation
  • Hydroquinone
  • Oxidation
  • Process chemistry

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

Fingerprint Dive into the research topics of 'A chemo-enzymatic expeditious route to racemic dihexanoyl (2R*,3R*,4R*)-dehydroxymethylepoxyquinomycin (DHMEQ), the precursor for lipase-catalyzed synthesis of the potent nuclear factor-κB inhibitor, (2 S,3S,4 S )-DHMEQ'. Together they form a unique fingerprint.

  • Cite this