Total synthesis of (R)-telomestatin

Takayuki Doi, Masahito Yoshida, Kazuo Shin-Ya, Takashi Takahashi

Research output: Contribution to journalArticle

97 Citations (Scopus)

Abstract

We have achieved a total synthesis of telomestatin, and its absolute configuration was determined to be (R). Coupling of cysteine-containing trisoxazole amine and serine-containing trisoxazole carboxylic acid, followed by macrocyclization, provided a 24-membered diamide. The seventh oxazole ring was formed by a Shin's procedure via dehydroamide. Cyclodehydration of a modified (R)-cysteine-(S-tBu) moiety using Kelly's method (PPh 3(O)-Tf2O) with anisole furnished (R)-telomestatin, whose CD spectrum was in good agreement with that of the natural product.

Original languageEnglish
Pages (from-to)4165-4167
Number of pages3
JournalOrganic letters
Volume8
Issue number18
DOIs
Publication statusPublished - 2006 Aug 31
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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