Construction of ansa-skeleton via intramolecular dötz benzannulation: Total synthesis of kendomycin

Yoko Saikawa, Kyosuke Tanaka, Masaya Nakata

研究成果: Article査読

2 被引用数 (Scopus)

抄録

Ansa-compounds have intriguing molecular structures and highly potent bioactivities. One of the ansa-compounds, kendomycin, has an oxa-metacyclophane skeleton with quinone methide core and a fully substituted tetrahydropyran ring. In contrast to a common synthetic strategy for construction of the ansa-skeleton via elongation of an alkyl chain from an aromatic core followed by macrocyclizalion, we challenged a new method for construction of the ansa-skeleton via simultaneous macrocyclizalion and benzannulation (using intramolecular Dötz benzannulation). Understanding the reactivity of various Fischer-type Ω-alkynyloxy chromium carbene complexes with kendomycin analogs 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.

本文言語English
ページ(範囲)1143-1153
ページ数11
ジャーナルYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
72
10
DOI
出版ステータスPublished - 2014 10 1

ASJC Scopus subject areas

  • 有機化学

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