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

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
53
4
DOI
出版ステータスPublished - 2012 1 25

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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