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一条化学酶促的快速路线，用于合成外消旋二己酰基(2R*,3R*,4R*)-脱羟甲基环氧喹霉素(DHMEQ)，它是脂肪酶催化合成强效核因子-κB抑制剂(2S,3S,4S)-DHMEQ的前体。

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.

作者信息

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

机构信息

Department of Pharmaceutical Science, Keio University, 1-5-30 Shibakoen, Tokyo 105-8512, Japan.

出版信息

Chem Pharm Bull (Tokyo). 2012;60(9):1220-3. doi: 10.1248/cpb.c12-00417.

DOI:10.1248/cpb.c12-00417
PMID:22976334
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.

摘要

为了大规模合成强效核因子（NF）-κB抑制剂（2S，3S，4S）-脱氢甲基环氧喹霉素（DHMEQ），开发了一种合成其相应外消旋前体二己酰基（2R*，3R*，4R*）-DHMEQ的新路线。通过同时使用对苯二酚和苯醌中间体，提高了总产率、重现性，减少了合成步骤，并降低了合成成本。

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