Toward the total synthesis of Luminamicin: Construction of 14-membered lactone framework possessing versatile enol ether moiety

Aoi Kimishima, Tomoyasu Hirose, Akihiro Sugawara, Takanori Matsumaru, Kaoru Nakamura, Ken Katsuyama, Masaki Toda, Hirokazu Takada, Rokuro Masuma, Satoshi Omura, Toshiaki Sunazuka

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Luminamicin (1) was found to exhibit selective antibacterial activity against anaerobic bacteria by our group in 1985. The concise structure of 14-membered lactone of 1 was synthesized. Construction of a versatile enol ether moiety was achieved by Stille cross coupling via hydrostanylation of the ethynyl ether, and a maleic anhydride moiety was derived from the furan constitution by the oxidation after the macrolactonization at a late-stage.

Original languageEnglish
Pages (from-to)2813-2816
Number of pages4
JournalTetrahedron Letters
Volume53
Issue number23
DOIs
Publication statusPublished - 2012 Jun 6
Externally publishedYes

Fingerprint

Lactones
Ether
Maleic Anhydrides
Anaerobic Bacteria
Constitution and Bylaws
Bacteria
Oxidation
luminamicin
furan

Keywords

  • 14-Membered macrolactone
  • Antianaerobic activity
  • Coloradocin
  • Conjugated enol ether
  • Luminamicin

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Toward the total synthesis of Luminamicin : Construction of 14-membered lactone framework possessing versatile enol ether moiety. / Kimishima, Aoi; Hirose, Tomoyasu; Sugawara, Akihiro; Matsumaru, Takanori; Nakamura, Kaoru; Katsuyama, Ken; Toda, Masaki; Takada, Hirokazu; Masuma, Rokuro; Omura, Satoshi; Sunazuka, Toshiaki.

In: Tetrahedron Letters, Vol. 53, No. 23, 06.06.2012, p. 2813-2816.

Research output: Contribution to journalArticle

Kimishima, A, Hirose, T, Sugawara, A, Matsumaru, T, Nakamura, K, Katsuyama, K, Toda, M, Takada, H, Masuma, R, Omura, S & Sunazuka, T 2012, 'Toward the total synthesis of Luminamicin: Construction of 14-membered lactone framework possessing versatile enol ether moiety', Tetrahedron Letters, vol. 53, no. 23, pp. 2813-2816. https://doi.org/10.1016/j.tetlet.2012.03.098
Kimishima, Aoi ; Hirose, Tomoyasu ; Sugawara, Akihiro ; Matsumaru, Takanori ; Nakamura, Kaoru ; Katsuyama, Ken ; Toda, Masaki ; Takada, Hirokazu ; Masuma, Rokuro ; Omura, Satoshi ; Sunazuka, Toshiaki. / Toward the total synthesis of Luminamicin : Construction of 14-membered lactone framework possessing versatile enol ether moiety. In: Tetrahedron Letters. 2012 ; Vol. 53, No. 23. pp. 2813-2816.
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