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

31 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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