The first total synthesis of hibarimicinone, a potent v-Src tyrosine kinase inhibitor

Kuniaki Tatsuta; Tomohiro Fukuda; Tatsuya Ishimori; Rearu Yachi; Shinpei Yoshida; Hiroshi Hashimoto; Seijiro Hosokawa

doi:10.1016/j.tetlet.2011.11.062

The first total synthesis of hibarimicinone, a potent v-Src tyrosine kinase inhibitor

Kuniaki Tatsuta, Tomohiro Fukuda, Tatsuya Ishimori, Rearu Yachi, Shinpei Yoshida, Hiroshi Hashimoto, Seijiro Hosokawa

先進理工学部

研究成果: Article › 査読

22 被引用数 (Scopus)

抄録

The first total synthesis of hibarimicinone has been achieved. The polyhydroxydecalin moieties (AB and GH rings) have been synthesized from sulfonylenone 4 derived from d-arabinose. The chiral biaryl 20 was coupled with two polyhydroxydecalins 11 by Michael-Dieckmann type condensation to give the eight rings system. Aromatization and oxidation with Ag ⁺ gave quinone 24, and the subsequential transannular etheration gave the hibarimicinone skeleton. Deprotection and tautomerization were performed in one pot to give hibarimicinone (1).

本文言語	English
ページ（範囲）	422-425
ページ数	4
ジャーナル	Tetrahedron Letters
巻	53
号	4
DOI	https://doi.org/10.1016/j.tetlet.2011.11.062
出版ステータス	Published - 2012 1 25

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

文献へのアクセス

10.1016/j.tetlet.2011.11.062

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引用スタイル

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AU - Yoshida, Shinpei

AU - Hashimoto, Hiroshi

AU - Hosokawa, Seijiro

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