穿越维维吲哚啉酮生物碱障碍课程时的经验教训。
Lessons Learned while Traversing the Welwitindolinone Alkaloids Obstacle Course.
作者信息
Bhat Vikram, Mackay James A, Rawal Viresh H
机构信息
Department of Chemistry, The University of Chicago, Chicago, IL 60637, USA.
出版信息
Tetrahedron. 2011 Dec 30;67(52):100997-10104. doi: 10.1016/j.tet.2011.09.088. Epub 2011 Sep 24.
Abstract
We recount several unexpected results observed in the course of our work toward the synthesis of welwitindolinone alkaloids. The surprising results provide an opportunity to refine one's understanding of the interplay between chemical structure and reactivity.
摘要
我们讲述了在合成维维吲哚啉酮生物碱的工作过程中观察到的几个意外结果。这些惊人的结果为完善人们对化学结构与反应性之间相互作用的理解提供了一个契机。
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本文引用的文献
1
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J Am Chem Soc. 2011 Oct 12;133(40):15797-9. doi: 10.1021/ja206538k. Epub 2011 Aug 11.
2
Stereocontrolled synthesis of 20,21-dihydro N-methylwelwitindolinone B isothiocyanate.立体控制合成 20,21-二氢 N-甲基威尔维蒂宁碱 B 异硫氰酸酯。
Chem Commun (Camb). 2011 Sep 14;47(34):9705-7. doi: 10.1039/c1cc13498a. Epub 2011 Jul 27.
3
Directed oxidative cyclizations to C2- or C4-positions of indole: efficient construction of the bicyclo[4.3.1]decane core of welwitindolinones.导向氧化环化至吲哚的 C2-或 C4-位：welwitindolinones 双环[4.3.1]癸烷核心的高效构建。
Org Lett. 2011 Jun 17;13(12):3214-7. doi: 10.1021/ol201122f. Epub 2011 May 26.
4
Total synthesis of N-methylwelwitindolinone D isonitrile.N-甲基威尔维啶酮 D 异腈的全合成。
J Am Chem Soc. 2011 Apr 20;133(15):5798-801. doi: 10.1021/ja201834u. Epub 2011 Mar 29.
5
Palladium-catalyzed conversion of aryl and vinyl triflates to bromides and chlorides.钯催化芳基和乙烯基三氟甲磺酸酯的溴化和氯化反应。
J Am Chem Soc. 2010 Oct 13;132(40):14076-8. doi: 10.1021/ja107481a.
6
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Tetrahedron. 2010 Aug 14;66(33):6647-6655. doi: 10.1016/j.tet.2010.04.131.
7
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8
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Chem Commun (Camb). 2009 Sep 14(34):5088-90. doi: 10.1039/b907761h. Epub 2009 May 26.
9
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10
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Org Lett. 2009 Nov 19;11(22):5330-3. doi: 10.1021/ol902173g.
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