Synthesis and biological evaluation of kendomycin and its analogues

Kyosuke Tanaka, Hiroshi Matsuyama, Masahito Watanabe, Yukiko Fujimori, Kodai Ishibashi, Tomohiro Ozawa, Tomoharu Sato, Yoko Saikawa, Masaya Nakata

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

Ansa compounds are gifts from microbes with intriguing molecular structures and highly potent bioactivities. One of the ansa compounds, kendomycin, has an oxa-metacyclophane skeleton with a quinone methide core and a fully substituted tetrahydropyran ring. Beyond a common synthetic strategy for construction of the ansa skeleton (i.e., elongation of an alkyl chain from an aromatic core followed by macrocyclization), we challenged a new method for construction of the ansa skeleton via simultaneous macrocyclization and benzannulation (using an intramolecular Dötz benzannulation). Understanding the reactivity of various Fischer-type ω-alkynyloxy chromium carbene complexes with kendomycin analogue syntheses led to achievement of the total synthesis of kendomycin. Investigations of structure-activity relationships revealed the need for an ansa skeleton for antimicrobial activity. Therefore, we envisage that this intramolecular Dötz benzannulation will enable divergent syntheses of ansa compounds which have important bioactive potential.

Original languageEnglish
Pages (from-to)9922-9947
Number of pages26
JournalJournal of Organic Chemistry
Volume79
Issue number21
DOIs
Publication statusPublished - 2014 Nov 7

ASJC Scopus subject areas

  • Organic Chemistry

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    Tanaka, K., Matsuyama, H., Watanabe, M., Fujimori, Y., Ishibashi, K., Ozawa, T., Sato, T., Saikawa, Y., & Nakata, M. (2014). Synthesis and biological evaluation of kendomycin and its analogues. Journal of Organic Chemistry, 79(21), 9922-9947. https://doi.org/10.1021/jo5015273