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, (2S,3S,4S)-DHMEQ.
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.
authors.affiliation: Department of Pharmaceutical Science, Keio University, 1-5-30 Shibakoen, Tokyo 105-8512, Japan.
authors.forename: Ryohei
authors.initials: R
authors.lastname: Kobayashi
authors.forename: Kengo
authors.initials: K
authors.lastname: Hanaya
authors.forename: Mitsuru
authors.initials: M
authors.lastname: Shoji
authors.forename: Kazuo
authors.initials: K
authors.lastname: Umezawa
authors.forename: Takeshi
authors.initials: T
authors.lastname: Sugai
mesh_terms: D001549:Benzamides / Q000138:chemical synthesis* / Q000378:metabolism; D016227:Benzoquinones / Q000138:chemical synthesis / Q000737:chemistry; D016956:Burkholderia cepacia / Q000201:enzymology; D002384:Catalysis; D003512:Cyclohexanones / Q000138:chemical synthesis* / Q000378:metabolism; D006873:Hydroquinones / Q000138:chemical synthesis / Q000737:chemistry; D020672:I-kappa B Proteins / Q000037:antagonists & inhibitors*; D008049:Lipase / Q000378:metabolism; D000072000:NF-KappaB Inhibitor alpha; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D001549:Benzamides; D016227:Benzoquinones; D003512:Cyclohexanones; D006873:Hydroquinones; D020672:I-kappa B Proteins; C464444:dehydroxymethylepoxyquinomicin; D000072000:NF-KappaB Inhibitor alpha; C004532:quinone; D008049:Lipase; C031927:hydroquinone