Total synthesis of elaiophylin (azalomycin B)

Kazunobu Toshima, Kuniaki Tatsuta, Mitsuhiro Kinoshita

Research output: Contribution to journalArticle

43 Citations (Scopus)

Abstract

Antibiotic elaiophylin 1a has been first synthesized by a convergent route involving aldol condensation between (5R,6R,7R)-5-0-[2′-deoxy-3′,4′-di-0-(dimethylisopropylsilyl)-α-L-fucopyranosyl]-6-ethyl-7-0-(diethylisopropylsilyl)-5,7-dihydroxy-3-octanone 3a and (7S,8S,15S, 16S) - (3E, 5E, 11E, 13E) -8,16-bis [ (1 ′R) -1′ -formylethyl] -7,15-dimethyl-1, 9-dioxacyclohexadeca-3,5, 11,13-tetraene-2,10-dione 4, followed by desilylation. The segments, 3a and 4, were synthesized from D-glucose and 2-deoxy-L-fucose.

Original languageEnglish
Pages (from-to)4741-4744
Number of pages4
JournalTetrahedron Letters
Volume27
Issue number39
DOIs
Publication statusPublished - 1986

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Glucose
Condensation
Anti-Bacterial Agents
elaiophylin
3-octanone
3-hydroxybutanal
2-deoxy-L-fucose

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Total synthesis of elaiophylin (azalomycin B). / Toshima, Kazunobu; Tatsuta, Kuniaki; Kinoshita, Mitsuhiro.

In: Tetrahedron Letters, Vol. 27, No. 39, 1986, p. 4741-4744.

Research output: Contribution to journalArticle

Toshima, Kazunobu ; Tatsuta, Kuniaki ; Kinoshita, Mitsuhiro. / Total synthesis of elaiophylin (azalomycin B). In: Tetrahedron Letters. 1986 ; Vol. 27, No. 39. pp. 4741-4744.
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