Synthesis of a Natural Chromenoquinone via the Diels–Alder Reaction of Pyranobenzyne and Furan

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  • Katakawa Kazuaki
    Department of Synthetic Organic Chemistry, Research Institute of Pharmaceutical Sciences, Musashino University
  • Sato Ayaka
    Department of Synthetic Organic Chemistry, Research Institute of Pharmaceutical Sciences, Musashino University
  • Iwasaki Mari
    Department of Synthetic Organic Chemistry, Research Institute of Pharmaceutical Sciences, Musashino University
  • Horikawa Tomofumi
    Department of Synthetic Organic Chemistry, Research Institute of Pharmaceutical Sciences, Musashino University
  • Kumamoto Takuya
    Department of Synthetic Organic Chemistry, Research Institute of Pharmaceutical Sciences, Musashino University

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  • Synthesis of a Natural Chromenoquinone <i>via</i> the Diels–Alder Reaction of Pyranobenzyne and Furan

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We describe the total synthesis of angular chromenoquinone 1 isolated from Conospermum plants. Iodophenol, a precursor of pyranobenzyne, was prepared by Claisen rearrangement of an iodoresorcinol derivative. Diels–Alder reaction of the pyranobenzyne and a substituted furan proceeded in low regioselectivity to afford desired 1 and its regioisomer.

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