Total synthesis of (+)-yatakemycin

Kentaro Okano, Hidetoshi Tokuyama, Tohru Fukuyama

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

A convergent total synthesis of (+)-yatakemycin was accomplished by a 20-step sequence in 13% overall yield. The regioselective ring opening of (S)-epichlorohydrin with a 2,6-dibromophenyllithium derivative enabled us to introduce a chiral carbon center, which was required for the stereoselective construction of the cyclopropane ring. The five aryl-nitrogen bonds in (+)-yatakemycin were constructed by a mild copper-mediated aryl amination that utilized the combination of CuI with CsOAc. The efficient and chemoselective debenzylation of aryl benzyl ether with BCl3 in the presence of pentamethylbenzene was developed. With these new methodologies, the subgram-scale synthesis of (+)-yatakemycin was achieved.

Original languageEnglish
Pages (from-to)296-309
Number of pages14
JournalChemistry - An Asian Journal
Volume3
Issue number2
DOIs
Publication statusPublished - 2008 Feb 1

Keywords

  • Aryl amination
  • Asymmetric synthesis
  • Copper
  • Total synthesis
  • Yatakemycin

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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