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

Fingerprint

Thiostrepton
Lactones
Anti-Bacterial Agents
Peptides
Acids
sulfinimine

Keywords

  • Dihydroxyisoleucine
  • Sulfinimines
  • Thiazolines
  • Thioamides
  • Thiostrepton

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthetic studies on thiostrepton family of peptide antibiotics : Synthesis of the pentapeptide segment containing dihydroxyisoleucine, thiazoline and dehydroamino acid. / Higashibayashi, Shuhei; Kohno, Mitsunori; Goto, Taiji; Suzuki, Kengo; Mori, Tomonori; Hashimoto, Kimiko; Nakata, Masaya.

In: Tetrahedron Letters, Vol. 45, No. 19, 03.05.2004, p. 3707-3712.

Research output: Contribution to journalArticle

Higashibayashi, Shuhei ; Kohno, Mitsunori ; Goto, Taiji ; Suzuki, Kengo ; Mori, Tomonori ; Hashimoto, Kimiko ; Nakata, Masaya. / Synthetic studies on thiostrepton family of peptide antibiotics : Synthesis of the pentapeptide segment containing dihydroxyisoleucine, thiazoline and dehydroamino acid. In: Tetrahedron Letters. 2004 ; Vol. 45, No. 19. pp. 3707-3712.
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