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Molecular Library Synthesis Using Complex Substrates: Expanding the Framework of Triterpenoids

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    Molecular Library Synthesis Using Complex Substrates: Expanding the Framework of Triterpenoids
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    Department of Chemistry, Case Western Reserve University, 10900 Euclid Avenue, Cleveland, Ohio 44106, United States
    *E-mail: [email protected]
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2013, 78, 2, 410–418
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jo302211f
    Published December 17, 2012
    Copyright © 2012 American Chemical Society
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    Abstract

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    The remodeling of a natural product core framework by means of diversity-oriented synthesis (DOS) is a valuable approach to access diverse/biologically relevant chemical space and to overcome the limitations of combinatorial-type compounds. Here we provide proof of principle and a thorough conformational analysis for a general strategy whereby the inherent complexity of a starting material is used to define the regio- and stereochemical outcomes of reactions in chemical library construction. This is in contrast to the traditional DOS logic employing reaction development and catalysis to drive library diversity.

    Copyright © 2012 American Chemical Society

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    Supporting Information

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    General experimental methods, mechanistic considerations for the formation of 10 and 11, conformational analysis of 4, 6, 16; complete ref 46; 1H and 13C NMR spectra of all new compounds, as well as HMQC, HMBC, COSY, and NOESY NMR spectra and the key COSY, HMBC, and NOESY correlations of compounds 6, 8–10, 12–15, 17, 19, and 20. This material is available free of charge via the Internet at http://pubs.acs.org.

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    Cited By

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    This article is cited by 26 publications.

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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2013, 78, 2, 410–418
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jo302211f
    Published December 17, 2012
    Copyright © 2012 American Chemical Society
    Request reuse permissions

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