Synthetic studies on thiostrepton family of peptide antibiotics: Synthesis of the pentapeptide segment containing dihydroxyisoleucine, thiazoline and dehydroamino acid

Shuhei Higashibayashi, Mitsunori Kohno, Taiji Goto, Kengo Suzuki, Tomonori Mori, Kimiko Hashimoto, Masaya Nakata

Research output: Contribution to journalArticle

32 Citations (Scopus)

Abstract

The dihydroxyisoleucine-, thiazoline- and dehydroamino acid-containing pentapeptide of the thiostrepton family of peptide antibiotics was synthesized, which featured the β-lactone opening by phenylselenylation, the vinylzinc addition to the chiral sulfinimine, the Wipf oxazoline-thiazoline conversion method and the oxidative syn-elimination of the phenylseleno group.

Original languageEnglish
Pages (from-to)3707-3712
Number of pages6
JournalTetrahedron Letters
Volume45
Issue number19
DOIs
Publication statusPublished - 2004 May 3

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Keywords

  • Dihydroxyisoleucine
  • Sulfinimines
  • Thiazolines
  • Thioamides
  • Thiostrepton

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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