Total synthesis of kendomycin featuring intramolecular dötz benzannulation

Kyosuke Tanaka, Masahito Watanabe, Kodai Ishibashi, Hiroshi Matsuyama, Yoko Saikawa, Masaya Nakata

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

One-step formation of the ansa-skeleton realized the synthesis of kendomycin, an ansa-type quinone methide. The Fischer carbene complex derived from the ansa-chain portion was subjected to the intramolecular Dötz benzannulation to afford the desired oxametacyclophane with exclusive regioselectivity. Subsequent Claisen rearrangement, ortho oxidation of the resulting phenol derivative, and mild transformation from p-quinone to p-quinone methide on a silica gel plate furnished kendomycin.

Original languageEnglish
Pages (from-to)1700-1703
Number of pages4
JournalOrganic Letters
Volume12
Issue number8
DOIs
Publication statusPublished - 2010 Apr 16

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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    Tanaka, K., Watanabe, M., Ishibashi, K., Matsuyama, H., Saikawa, Y., & Nakata, M. (2010). Total synthesis of kendomycin featuring intramolecular dötz benzannulation. Organic Letters, 12(8), 1700-1703. https://doi.org/10.1021/ol100229f