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, (2S,3S,4S)-DHMEQ

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

doi:10.1248/cpb.c12-00417

Notes

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, (2S,3S,4S)-DHMEQ

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

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Keywords: dehydroxymethylepoxyquinomycin, process chemistry, hydroquinone, oxidation, benzoquinone, epoxidation

JOURNAL FREE ACCESS

2012 Volume 60 Issue 9 Pages 1220-1223

DOI https://doi.org/10.1248/cpb.c12-00417

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Abstract

In order to synthesize the potent nuclear factor (NF)-κB inhibitor, (2S,3S,4S)-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.

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