Use of Emerging C-H Functionalization Methods to Implement Strategies for the Divergent Total Syntheses of Bridged Polycyclic Natural Products

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  • 千成 恒
    Department of Chemistry, University of California-Berkeley Ōmura Satoshi Memorial Institute and Graduate School of Infection Control Sciences, Kitasato University
  • Sarpong Richmond
    Department of Chemistry, University of California-Berkeley

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<p>Carbon-hydrogen (C-H) bonds are ubiquitous in complex natural products. Over the past three decades, many methods to convert C-H bonds distal from functional groups, which were generally considered inert, have been developed. These advances now enable selective peripheral functionalizations at a late-stage. The direct engagement of traditionally unreactive C-H bonds in reactions expands chemical space by reducing functional group interconversions. As such, C-H functionalization serves as a powerful tool in medicinal and agrocultural chemistry as well as in the total synthesis of natural products where diversification to a broad array of compounds from a common intermediate is often desired. In this Account, we detail the thought processes and design principles that relied on emerging methods for C-H functionalization to prepare a wide range of bridged, polycyclic, natural products in the cephalotane and longibornane families from a common intermediate in each case.</p>

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