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

Fingerprint

Lipase
Costs and Cost Analysis
Costs
benzoquinone
hydroquinone

Keywords

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

ASJC Scopus subject areas

  • Drug Discovery
  • Chemistry(all)

Cite this

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title = "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",
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.",
keywords = "Benzoquinone, Dehydroxymethylepoxyquinomycin, Epoxidation, Hydroquinone, Oxidation, Process chemistry",
author = "Ryohei Kobayashi and Kengo Hanaya and Mitsuru Shoji and Kazuo Umezawa and Takeshi Sugai",
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AU - Kobayashi, Ryohei

AU - Hanaya, Kengo

AU - Shoji, Mitsuru

AU - Umezawa, Kazuo

AU - Sugai, Takeshi

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AB - 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.

KW - Benzoquinone

KW - Dehydroxymethylepoxyquinomycin

KW - Epoxidation

KW - Hydroquinone

KW - Oxidation

KW - Process chemistry

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