Total Synthesis of (-)-Morphine

Hirotatsu Umihara; Satoshi Yokoshima; Masayuki Inoue; Tohru Fukuyama

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Total Synthesis of (-)-Morphine

机译：（ - ） - 吗啡的总合成

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Asymmetric total synthesis of (-)-morphine has been accomplished in 18 steps from commercially available 7-methoxy-2-tetralone. Our synthesis features a simple transformation from a readily prepared chiral intermediate, construction of the E-ring by acid-mediated cyclization, and singlet oxygen-mediated manipulation of the C-ring. Transformation of the final stage involves construction of the morphinan skeleton by means of 1,6-addition of in situ generated secondary amine.

机译：（ - ） - 吗啡的不对称总合成已在商业上可获得的7-甲氧基-2-Tetralone完成18步。我们的合成特征来自容易制备的手性中间，通过酸介导的环化构造的易于制备的手性中间化，并单线氧介导的C环的操纵。最终阶段的转化涉及通过1,6-加入原位生成的二胺构建变质骨架。

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来源
《Chemistry: A European journal》 |2017年第29期|共3页
作者
Hirotatsu Umihara; Satoshi Yokoshima; Masayuki Inoue; Tohru Fukuyama;
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作者单位

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 Nagoya Aichi 464-8601 (Japan);

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 Nagoya Aichi 464-8601 (Japan);

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原文格式 PDF
正文语种 eng
中图分类应用化学;
关键词
aldol reaction; conjugate addition; morphine; singlet oxygen; total synthesis;

机译：醛醇反应;共轭添加;吗啡;单线氧;总合成;

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专利

1. Total Synthesis of (-)-Morphine [J] . Hirotatsu Umihara, Satoshi Yokoshima, Masayuki Inoue, Chemistry: A European journal . 2017,第29期

机译：（ - ） - 吗啡的总合成
2. TOTAL SYNTHESIS OF (±)-MORPHINE [J] . Kenji Uchida, Satoshi Yokoshima, Toshiyuki Kan Heterocycles: An International Journal for Reviews and Communications in Heterocyclic Chemistry . 2009,第2期

机译：总合成（±）-吗啡
3. Total synthesis of (+/-)-morphine [J] . Uchida K, Yokoshima S, Kan T, Organic letters . 2006,第23期

机译：（+/-）-吗啡的全合成
4. Synthesis, Characterization, and In Vitro Studies of a Morphine-based Poly(anhydride-ester) [C] . Roselin Rosario-Meléndez, Roberto Delgado-Rivera, Lei Yu PMSE Symposia . 2011

机译：基于吗啡的聚（酸酐）的合成，表征和体外研究
5. Applications of dihydroarenediols to chemoenzymatic synthesis: Approaches to total synthesis of morphine alkaloids. [D] . Finn, Kevin J. 2006

机译：二氢芳烃在化学酶法合成中的应用：吗啡生物碱的全合成方法。
6. Enantioselective synthesis of cis-hydrobenzofurans bearing all-carbon quaternary stereocenters and application to total synthesis of (‒)-morphine [O] . Qing Zhang, Fu-Min Zhang, Chang-Sheng Zhang, -1

机译：具有全碳四级立体中心的顺式对苯并呋喃的对映选择性合成及其在（‒）-吗啡的全合成中的应用
7. Enantioselective synthesis of cis-hydrobenzofurans bearing all-carbon quaternary stereocenters and application to total synthesis of (‒)-morphine [O] . Qing Zhang, Fu-Min Zhang, Chang-Sheng Zhang, 2019

机译：含有全碳季型立体封闭器的顺式氢苯甲苯酚的映选择性合成及其在（ - ） - 吗啡的总合成中

Total Synthesis of (-)-Morphine

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