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  • A Concise Route to Dihydrobenzo[b]furans: Formal Total Synthesis of (+)-Lithospermic Acid

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    Author(s)
    Fischer, Joshua
    Savage, G Paul
    Coster, Mark J
    Griffith University Author(s)
    Coster, Mark J.
    Fischer, Joshua
    Year published
    2011
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    Abstract
    A sequence of Sonogashira coupling, Pd(II)-catalyzed carbonylative annulation, and benzofuran reduction (Mg, MeOH, NH4Cl) provides a convergent and modular synthetic route to trans-2-aryl-2,3-dihydrobenzo[b]furan-3-carboxylates, which are a structural feature of numerous biologically active natural products. This versatile strategy was applied to the formal total synthesis of the anti-HIV natural product (+)-lithospermic acid.A sequence of Sonogashira coupling, Pd(II)-catalyzed carbonylative annulation, and benzofuran reduction (Mg, MeOH, NH4Cl) provides a convergent and modular synthetic route to trans-2-aryl-2,3-dihydrobenzo[b]furan-3-carboxylates, which are a structural feature of numerous biologically active natural products. This versatile strategy was applied to the formal total synthesis of the anti-HIV natural product (+)-lithospermic acid.
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    Journal Title
    Organic Letters
    Volume
    13
    Issue
    13
    DOI
    https://doi.org/10.1021/ol201130h
    Copyright Statement
    This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright 2011 American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/ol201130h.
    Subject
    Chemical sciences
    Organic chemical synthesis
    Publication URI
    http://hdl.handle.net/10072/42743
    Collection
    • Journal articles

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