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    Total Synthesis of (±)-Cis-Trikentrin B via Intermolecular 6,7-Indole Aryne Cycloaddition and Stille Cross-Coupling

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    Brown&Buszek_Total_Synthesis.pdf (940.5Kb)
    Issue Date
    2014-09-30
    Author
    Chandrasoma, Nalin
    Brown, Neil
    Brassfield, Allen
    Nerurkar, Alok
    Suarez, Susana
    Buszek, Keith R.
    Publisher
    Elsevier
    Type
    Article
    Article Version
    Scholarly/refereed, author accepted manuscript
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    Abstract
    An efficient total synthesis of the annulated indole natural product (±)-cis-trikentrin B was accomplished by means of a regioselectively generated 6,7-indole aryne cycloaddition via selective metal-halogen exchange from a 5,6,7-tribromoindole. The unaffected C-5 bromine was subsequently used for a Stille cross-coupling to install the butenyl side chain and complete the synthesis. This strategy provides rapid access into the trikentrins and the related herbindoles, and represents another application of this methodology to natural products total synthesis. The required 5,6,7-indole aryne precursor was prepared using the Leimgruber-Batcho indole synthesis.
    Description
    From PMC: This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final citable form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain.
    URI
    http://hdl.handle.net/1808/15383
    DOI
    https://doi.org/10.1016/j.tetlet.2012.11.125
    Collections
    • Chemistry Scholarly Works [610]
    Citation
    Total Synthesis of (±)-Cis-Trikentrin B via Intermolecular 6,7-Indole Aryne Cycloaddition and Stille Cross-Coupling Nalin Chandrasoma, Neil Brown, Allen Brassfield, Alok Nerurkar, Susana Suarez, Keith R. Buszek Tetrahedron Lett. Author manuscript; available in PMC 2014 September 30. Published in final edited form as: Tetrahedron Lett. 2013 February 20; 54(8): 913–917. http://dx.doi.org.10.1016/j.tetlet.2012.11.125

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    KU Libraries
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    785-864-8983

    KU Libraries
    1425 Jayhawk Blvd
    Lawrence, KS 66045
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    Contact KU ScholarWorks
    785-864-8983
    KU Libraries
    1425 Jayhawk Blvd
    Lawrence, KS 66045
    785-864-8983

    KU Libraries
    1425 Jayhawk Blvd
    Lawrence, KS 66045
    Image Credits
     

     

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