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Microwave-Based Reaction Screening: Tandem Retro-Diels Alder/Diels-Alder Cycloadditions of o-Quinol Dimers

  1. Author:
    Dong, S. W.
    Cahill, K. J.
    Kang, M. I.
    Colburn, N. H.
    Henrich, C. J.
    Wilson, J. A.
    Beutler, J. A.
    Johnson, R. P.
    Porco, J. A.

  2. Author Address

    [Cahill, KJ; Johnson, RP] Univ New Hampshire, Dept Chem, Durham, NH 03824 USA. [Dong, SW; Porco, JA] Boston Univ, Dept Chem, Boston, MA 02215 USA. [Dong, SW; Porco, JA] Boston Univ, Ctr Chem Methodol & Lib Dev CMLD BU, Boston, MA 02215 USA. [Kang, MI; Colburn, NH; Henrich, CJ; Wilson, JA; Beutler, JA] NCI, Ctr Canc Res, Lab Canc Prevent, Frederick, MD 21702 USA. [Kang, MI; Colburn, NH; Henrich, CJ; Wilson, JA; Beutler, JA] NCI, Ctr Canc Res, Mol Targets Lab, Frederick, MD 21702 USA.;Johnson, RP (reprint author), Univ New Hampshire, Dept Chem, Durham, NH 03824 USA;richard.johnson@unh.edu porco@bu.edu
    1. Year: 2011
    2. Date: Nov
  2. Journal: Journal of Organic Chemistry
    1. 76
    2. 21
    3. Pages: 8944-8954
  4. Type of Article: Article
  5. ISSN: 0022-3263
  1. Abstract:

    We have accomplished a parallel screen of cycloaddition partners for o-quinols utilizing a plate-based microwave system. Microwave irradiation improves the efficiency of retro-Diels-Alder/Diels-Alder cascades of o-quinol dimers which generally proceed in a diastereoselective fashion. Computational studies indicate that asynchronous transition states are favored in Diels-Alder cycloadditions of o-quinols. Subsequent biological evaluation of a collection of cycloadducts has identified an inhibitor of activator protein-1 (AP-1), an oncogenic transcription factor.

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External Sources

  1. View Full Text
  2. DOI: 10.1021/jo201658y
  3. View record in Web of Science®
  4. WOS: 000296206400036

Library Notes

  1. Fiscal Year: FY2011-2012
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