Catalysis-based enantioselective total synthesis of the macrocyclic spermidine alkaloid isooncinotine

Scheiper B; Glorius F; Leitner A; Furstner A

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Catalysis-based enantioselective total synthesis of the macrocyclic spermidine alkaloid isooncinotine

机译：大环亚精胺生物碱异西诺丁碱的催化对映选择性全合成

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摘要

A concise and efficient total synthesis of the spermidine alkaloid (-)-isooncinotine (1) incorporating a 22-membered lactam ring is outlined. The approach is largely catalysis-based, involving a selective iron-catalyzed alkyl-aryl cross-coupling reaction of a difunctionalized pyridine substrate, a heterogeneous asymmetric hydrogenation step to set the chiral center of the target, and a highly integrated ring-closing metathesis/hydrogenation sequence to forge the saturated macrocyclic edifice in a single operation.

机译：概述了一个精简而有效的全合成亚精胺生物碱（-）-异西诺丁碱（1）的22元内酰胺环。该方法主要是基于催化的，涉及双官能化吡啶底物的选择性铁催化的烷基-芳基交叉偶联反应，设置目标手性中心的非均相不对称氢化步骤以及高度集成的闭环复分解/一次加氢即可形成饱和的大环大厦。

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来源
《Proceedings of the National Academy of Sciences of the United States of America》 |2004年第33期|p. 11960-11965|共6页
作者
Scheiper B; Glorius F; Leitner A; Furstner A;
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作者单位

Max Planck Inst Kohlenforsch, D-45470 Mulheim, Ruhr, Germany;

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收录信息美国《科学引文索引》(SCI);美国《生物学医学文摘》(MEDLINE);美国《化学文摘》(CA);
原文格式 PDF
正文语种 eng
中图分类自然科学总论;
关键词
CROSS-COUPLING REACTIONS; OLEFIN METATHESIS; ONCINOTIS-TENUILOBA; RUTHENIUM CARBENE; CHEMISTRY; NEOONCINOTINE; HYDROGENATION; DERIVATIVES; POLYAMINES; COMPLEXES;

机译：交叉偶联;烯烃复分解;天青-特诺洛巴;钌碳;化学;新蛋氨酸;加氢;衍生物;聚酰胺;复合物;

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1. The Macrocyclic Spermidine Alkaloid (-)-(S)-Neoperiphylline: Revision of the Structure Based on the Total Synthesis [J] . Sergey A. Sergeyev, Manfred Hesse Helvetica chimica acta . 2003,第2期

机译：大环亚精胺生物碱（-）-（S）-神经叶茶碱：基于全合成的结构修订
2. Catalysis-based enantioselective total synthesis of myxothiazole Z,(14S)-melithiazole G and (14S)-cystothiazole F [J] . Aude Colon, Thomas J. Hoffman, Julian Gebauer, Chemical Communications . 2012,第85期

机译：催化合成对甲噻唑Z，（14S）-美拉沙唑G和（14S）-巯基噻唑F的对映选择性全合成
3. A Novel Synthesis of teh Macrocyclic Spermidine Alkaloid (+)-(S)-Dihydroperiphylline [J] . Sergey A.Sergeyev, Manfred Hesse Helvetica chimica acta . 2002,第1期

机译：大环亚精胺生物碱（+）-（S）-双氢茶碱的新型合成方法
4. Asymmetric Total Synthesis, Stereochemical Stability and Cancer Cell Killing Effects of Stemona Alkaloids [C] . Takayuki Iwata, Satoshi Fujita, Taishi Tomiyama 日本化学会春季年会講演予稿集 . 2018

机译：不对称的全合成，立体化学稳定性和癌细胞杀菌作用对斯莫纳生物碱的杀伤作用
5. Catalytic enantioselective synthesis of amino acids and macrocyclic peptides: Application towards an enantioselective total synthesis of complestatin. [D] . Kuntz, Kevin Wayne. 2002

机译：氨基酸和大环肽的催化对映选择性合成：对complestatin的对映选择性全合成的应用。
6. Natural Product Synthesis Special Feature: Catalysis-based enantioselective total synthesis of the macrocyclic spermidine alkaloid isooncinotine [O] . Bodo Scheiper, Frank Glorius, Andreas Leitner, 2004

机译：天然产物合成的特殊功能：基于催化的对映选择性全合成大环亚精胺生物碱异西诺丁碱
7. Catalysis-based enantioselective total synthesis of the macrocyclic spermidine alkaloid isooncinotine [O] . Scheiper, Bodo, Glorius, Frank, Leitner, Andreas, 2004

机译：大环亚精胺生物碱异西诺丁碱的催化对映选择性全合成

Catalysis-based enantioselective total synthesis of the macrocyclic spermidine alkaloid isooncinotine

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