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

研究成果: Article査読

6 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)9922-9947
ページ数26
ジャーナルJournal of Organic Chemistry
79
21
DOI
出版ステータスPublished - 2014 11 7

ASJC Scopus subject areas

  • 有機化学

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