Synthesis and Structure Revision of Goupiolone A: A Benzotropolone Natural Product

Authors

  • Nobuaki Fukui,

    1. Department of Chemistry, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo 152-8551, Japan, (fax: +81-3-5734-2788)
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  • Ken Ohmori,

    1. Department of Chemistry, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo 152-8551, Japan, (fax: +81-3-5734-2788)
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  • Keisuke Suzuki

    Corresponding author
    1. Department of Chemistry, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo 152-8551, Japan, (fax: +81-3-5734-2788)
    • Department of Chemistry, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo 152-8551, Japan, (fax: +81-3-5734-2788)

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Abstract

Goupiolone A, a benzotropolone natural product, has been synthesized by assembling a benzocyclobutene derivative and a silyl-substituted cyclopropane unit, followed by thermal ring enlargement. The synthetic sample did not correspond to the reported data. On the basis of biogenetic considerations, an alternative structure with a catechol moiety was proposed, and the synthesis established it as the correct structure.

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