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Synthesis of Polycyclic Structures by the Diels−Alder Reaction of Inner-Outer-Ring 1,3-Bis(trimethylsilyloxy)dienes
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    Synthesis of Polycyclic Structures by the Diels−Alder Reaction of Inner-Outer-Ring 1,3-Bis(trimethylsilyloxy)dienes
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    Departamento de Química Fundamental, Universidade da Coruña, E-15071 A Coruña, Spain
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2001, 66, 4, 1395–1402
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    https://doi.org/10.1021/jo0015319
    Published January 17, 2001
    Copyright © 2001 American Chemical Society

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    A Diels−Alder reaction of novel inner-outer-ring 1,3-silyloxydienes 58 with a variety of dienophiles to afford highly functionalized polycyclic structures is reported. The inner-outer-ring 1,3-silyloxydienes 58 containing five- to seven-membered carbocyclic and heterocyclic rings were prepared in a single reaction vessel from 2-acetylcyclocarbonyls in quantitative yields. The Diels−Alder reaction with 1,4-benzoquinone (BQ), dimethyl acetylenedicarboxylate (DMAD), and methyl vinyl ketone (MVK) proceeded smoothly at room temperature, affording functionalized polycyclic naphthols, phenols, and enones with high regioselectivity and good yields (39−75%). Moreover, dienes 58 also reacted in a hetero-Diels−Alder reaction with benzaldehyde (BA) and N-benzylideneaniline (NBA) in the presence of catalytic amounts of ZnCl2, affording substituted polycyclic pyranones and pyridinones in good yields (40−93%). Overall, our synthetic strategy provides straightforward access to an interesting set of polycyclic structures useful for natural and nonnatural product synthesis.

    Copyright © 2001 American Chemical Society

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    1H NMR and 13C NMR for all new compounds. This material is available free of charge via the Internet at http://pubs.acs.org.

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    27. Jose Perez Sestelo, Maria del Mar Real, Luis A. Sarandeses. ChemInform Abstract: Synthesis of Polycyclic Structures by the Diels—Alder Reaction of Inner‐Outer‐Ring 1,3‐Bis(trimethylsilyloxy)dienes.. ChemInform 2001, 32 (25) https://doi.org/10.1002/chin.200125038

    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2001, 66, 4, 1395–1402
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jo0015319
    Published January 17, 2001
    Copyright © 2001 American Chemical Society

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