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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.

chemical and pharmaceutical bulletin/chemical and pharmaceutical bulletin

A Chemo-Enzymatic Expeditious Route to Racemic Dihexanoyl (2&lt;i&gt;R&lt;/i&gt;*,3&lt;i&gt;R&lt;/i&gt;*,4&lt;i&gt;R&lt;/i&gt;*)-Dehydroxymethylepoxyquinomycin (DHMEQ), the Precursor for Lipase-Catalyzed Synthesis of the Potent Nuclear Factor-κB Inhibitor, (2&lt;i&gt;S&lt;/i&gt;,3&lt;i&gt;S&lt;/i&gt;,4&lt;i&gt;S&lt;/i&gt;)-DHMEQ