（-）-羟考酮的合成。
Synthesis of (-)-oxycodone.
作者信息
Kimishima Atsushi, Umihara Hirotatsu, Mizoguchi Akihiro, Yokoshima Satoshi, Fukuyama Tohru
机构信息
†Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
‡Graduate School of Pharmaceutical Sciences, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8601, Japan.
出版信息
Org Lett. 2014 Dec 5;16(23):6244-7. doi: 10.1021/ol503175n. Epub 2014 Nov 25.
Our novel synthetic route to (-)-oxycodone, a semisynthetic opioid analgesic, features a palladium-catalyzed direct intramolecular arylation of an aryl bromide, oxidative dearomatization of a dihydrophenanthrenol, formation of a benzylic quaternary carbon by an intramolecular Michael addition of a malonate moiety, and construction of the morphinan skeleton via a Hofmann rearrangement/lactamization cascade.
我们合成半合成阿片类镇痛药（-）-羟考酮的新路线的特点包括：钯催化芳基溴的直接分子内芳基化、二氢菲醇的氧化脱芳构化、丙二酸酯部分通过分子内迈克尔加成形成苄基季碳，以及通过霍夫曼重排/内酰胺化级联构建吗啡喃骨架。
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