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

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

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).

Original languageEnglish
Pages (from-to)422-425
Number of pages4
JournalTetrahedron Letters
Volume53
Issue number4
DOIs
Publication statusPublished - 2012 Jan 25

Keywords

  • Hauser annulation
  • Hibarimicin
  • Hibarimicinone
  • Thiolactone
  • Total synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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