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抱歉打断一下:对费舍尔经典反应的一种改进,用于杂环和天然产物的合成。

Pardon the Interruption: A Modification of Fischer's Venerable Reaction for the Synthesis of Heterocycles and Natural Products.

作者信息

Susick Robert B, Morrill Lucas A, Picazo Elias, Garg Neil K

机构信息

Department of Chemistry and Biochemistry, University of California, Los Angeles, 607 Charles E. Young Drive East, Los Angeles, CA 90095, USA.

出版信息

Synlett. 2017;28(1):1-11. doi: 10.1055/s-0036-1588372.

Abstract

This account provides an overview of our laboratory's studies of an unusual variant of the Fischer indolization reaction. We describe the discovery of the so-called 'interrupted Fischer indolization' and the development of the reaction from a methodological standpoint. In addition, our efforts to evaluate and apply this methodology in the context of akuammiline alkaloid total synthesis are discussed.

摘要

本报告概述了我们实验室对费歇尔吲哚合成反应一种不寻常变体的研究。我们描述了所谓“间断费歇尔吲哚合成”的发现以及从方法学角度该反应的发展。此外,还讨论了我们在阿库胺类生物碱全合成背景下评估和应用该方法的努力。

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Org Lett. 2016 Apr 1;18(7):1670-3. doi: 10.1021/acs.orglett.6b00536. Epub 2016 Mar 24.
5
Asymmetric Total Syntheses of Aspidodasycarpine, Lonicerine, and the Proposed Structure of Lanciferine.
J Am Chem Soc. 2016 Mar 30;138(12):3982-5. doi: 10.1021/jacs.6b00764. Epub 2016 Mar 18.
6
Total Synthesis of (±)-Strictamine.
Angew Chem Int Ed Engl. 2016 Mar 1;55(10):3500-3. doi: 10.1002/anie.201511638. Epub 2016 Feb 4.
7
Synthetic Strategies toward Natural Products Containing Contiguous Stereogenic Quaternary Carbon Atoms.
Angew Chem Int Ed Engl. 2016 Mar 18;55(13):4156-86. doi: 10.1002/anie.201507549. Epub 2016 Feb 2.
8
Enantioselective Total Syntheses of Akuammiline Alkaloids (+)-Strictamine, (-)-2(S)-Cathafoline, and (-)-Aspidophylline A.
J Am Chem Soc. 2016 Feb 3;138(4):1162-5. doi: 10.1021/jacs.5b12880. Epub 2016 Jan 19.
10
Recent Advances on the Total Syntheses of Communesin Alkaloids and Perophoramidine.
Chemistry. 2015 Nov 9;21(46):16318-43. doi: 10.1002/chem.201501735. Epub 2015 Sep 10.

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