Synthesis of (+)-Obtusenyne

Mak SYF; Curtis NR; Payne AN; Congreve MS; Wildsmith AJ; Francis CL; Davies JE; Pascu SI; Burton JW; Holmes AB

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Synthesis of (+)-Obtusenyne

机译：（+）-奥布妥烯的合成

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An enantioselective synthesis of the halogenated medium-ring ether natural product (+)-obtusenyne is reported which uses the ring expansion of a seven-membered ketene acetal by means of a Claisen rearrangement to construct the core nine-membered oxygen heterocycle. The trans substituents across the ether linkage were established by using a transition-metalcatalyzed intramolecular hydrosilation reaction of an exo-cyclic enol ether. In addition, a formal synthesis of ent-obtusenyne from 2-deoxy-D-ribose is reported. A number of interesting points regarding the chemistry of medium-ring oxygen heterocycles are highlighted.

机译：据报道，卤化的中环醚天然产物（+）-ob烯炔的对映选择性合成是通过克莱森重排利用七元乙烯酮缩醛的扩环来构建核心的九元氧杂环。通过使用环外环烯醇醚的过渡金属催化的分子内硅氢化反应，建立了跨醚键的反式取代基。另外，据报道由2-脱氧-D-核糖正式合成对-奥布他汀。突出了有关中环氧杂环的化学反应的许多有趣的观点。

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来源
《Chemistry: A European journal》 |2008年第9期|共19页
作者
Mak SYF; Curtis NR; Payne AN; Congreve MS; Wildsmith AJ; Francis CL; Davies JE; Pascu SI; Burton JW; Holmes AB;
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正文语种 eng
中图分类化学;
关键词
Claisen rearrangement; hydrosilation; medium rings; natural products; total synthesis; MEDIUM RING ETHERS; ENANTIOSELECTIVE TOTAL-SYNTHESIS; 2-DEOXY L-RIBOSE; ORGANIC-SYNTHESIS; CLAISEN REARRANGEMENT; STEREOSELECTIVE SYNTHESIS; INTRAMOLECULAR HYDROSILATION; EFFICIENT SYNTHESIS; CARBON BOND; L-ARABINOSE;

机译：克莱森重排;硅氢化;中环;天然产物;全合成;中环醚;对映选择性全合成;2-脱氧L-核糖;有机合成;Claisen重排;立体选择性合成;分子内加氢;核键;高效-阿拉伯糖;

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1. Determination of the absolute configurations of Norte's obtusenynes by total syntheses of (12R,13R)-(-)- and (12S,13R)-(+)-obtusenynes [J] . Awakura D., Murai A., Fujiwara K. Chemistry Letters . 1999,第6期

机译：通过（12R，13R）-（-）-和（12S，13R）-（+）-ob烯酮的全合成来确定Norte tus烯酮的绝对构型
2. Total Synthesis of (-)-12,13-epi-Obtusenyne [J] . Toshio Suzuki, Nobuyuki Yoshino, Toshiyuki Uemura Chemistry Letters . 2007,第2期

机译：（-）-12,13-epi-Obtusenyne的全合成
3. Total synthesis of (+)-obtusenyne [J] . Toshiyuki Uemura, Toshio Suzuki, Naohiro Onodera Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2007,第26期

机译：（+）-obtusenyne的全合成
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Synthesis of (+)-Obtusenyne

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