Literature DB >> 23540731

Copper-catalyzed diastereoselective arylation of tryptophan derivatives: total synthesis of (+)-naseseazines A and B.

Madeleine E Kieffer1, Kangway V Chuang, Sarah E Reisman.   

Abstract

A copper-catalyzed arylation of tryptophan derivatives is reported. The reaction proceeds with high site- and diastereoselectivity to provide aryl pyrroloindoline products in one step from simple starting materials. The utility of this transformation is highlighted in the five-step syntheses of the natural products (+)-naseseazine A and B.

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Year:  2013        PMID： 23540731      PMCID： PMC3662218          DOI： 10.1021/ja4023557

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  44 in total

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5.  Cyclopropylazetoindolines as precursors to C(3)-quaternary-substituted indolines.

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Authors:  Justin Kim; James A Ashenhurst; Mohammad Movassaghi
Journal:  Science       Date:  2009-04-10       Impact factor: 47.728

8.  A Copper-Catalyzed Arylation of Tryptamines for the Direct Synthesis of Aryl Pyrroloindolines.

Authors:  Madeleine E Kieffer; Kangway V Chuang; Sarah E Reisman
Journal:  Chem Sci       Date:  2012-11       Impact factor: 9.825

9.  Total synthesis of (+/-)-psychotrimine.

Authors:  Timothy Newhouse; Phil S Baran
Journal:  J Am Chem Soc       Date:  2008-07-26       Impact factor: 15.419

10.  Activator-free olefin oligomerization and isomerization reactions catalyzed by an air- and water-tolerant Wacker oxidation intermediate.

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Journal:  Angew Chem Int Ed Engl       Date:  2012-09-03       Impact factor: 15.336
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  24 in total

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Journal:  J Am Chem Soc       Date:  2016-01-19       Impact factor: 15.419

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Authors:  David E Stephens; Oleg V Larionov
Journal:  European J Org Chem       Date:  2014-06-01

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Journal:  J Am Chem Soc       Date:  2017-11-20       Impact factor: 15.419

6.  Enantioselective Synthesis of Pyrroloindolines via Noncovalent Stabilization of Indole Radical Cations and Applications to the Synthesis of Alkaloid Natural Products.

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8.  Enantioselective α-alkenylation of aldehydes with boronic acids via the synergistic combination of copper(II) and amine catalysis.

Authors:  Jason M Stevens; David W C MacMillan
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9.  Concise Total Synthesis of (+)-Luteoalbusins A and B.

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10.  Concise Total Synthesis of (+)-Bionectins A and C.

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Journal:  Chem Sci       Date:  2013-08       Impact factor: 9.825
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