Synthetic studies on thiostrepton family of peptide antibiotics: Synthesis of the dihydroquinoline portion of thiostrepton, the siomycins, and the thiopeptins

Tomonori Mori, Yukiko Satouchi, Hiraku Tohmiya, Shuhei Higashibayashi, Kimiko Hashimoto, Masaya Nakata

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

Synthesis of the dihydroquinoline portion of thiostrepton, the siomycins, and the thiopeptins, members of the thiostrepton family of peptide antibiotics, has been achieved featuring the one-pot olefination via the Matsumura- Boekelheide rearrangement "using trifluoromethanesulfonic anhydride and triethylamine" and the stereoselective addition reaction controlled by the stereocenter of the peri-position.

Original languageEnglish
Pages (from-to)6417-6422
Number of pages6
JournalTetrahedron Letters
Volume46
Issue number38
DOIs
Publication statusPublished - 2005 Sep 19

Fingerprint

Thiostrepton
Anti-Bacterial Agents
Peptides
Addition reactions
Anhydrides
siomycin
thiopeptin

Keywords

  • Dihydroquinoline
  • Matsumura-Boekelheide rearrangement
  • Siomycins
  • Stereoselective addition
  • Thiostrepton

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthetic studies on thiostrepton family of peptide antibiotics : Synthesis of the dihydroquinoline portion of thiostrepton, the siomycins, and the thiopeptins. / Mori, Tomonori; Satouchi, Yukiko; Tohmiya, Hiraku; Higashibayashi, Shuhei; Hashimoto, Kimiko; Nakata, Masaya.

In: Tetrahedron Letters, Vol. 46, No. 38, 19.09.2005, p. 6417-6422.

Research output: Contribution to journalArticle

Mori, Tomonori ; Satouchi, Yukiko ; Tohmiya, Hiraku ; Higashibayashi, Shuhei ; Hashimoto, Kimiko ; Nakata, Masaya. / Synthetic studies on thiostrepton family of peptide antibiotics : Synthesis of the dihydroquinoline portion of thiostrepton, the siomycins, and the thiopeptins. In: Tetrahedron Letters. 2005 ; Vol. 46, No. 38. pp. 6417-6422.
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