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

doi:10.1016/j.tetlet.2012.03.098

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 journal › Article

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 language	English
Pages (from-to)	2813-2816
Number of pages	4
Journal	Tetrahedron Letters
Volume	53
Issue number	23
DOIs	https://doi.org/10.1016/j.tetlet.2012.03.098
Publication status	Published - 2012 Jun 6
Externally published	Yes

Keywords

14-Membered macrolactone
Antianaerobic activity
Coloradocin
Conjugated enol ether
Luminamicin

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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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, 53(23), 2813-2816. https://doi.org/10.1016/j.tetlet.2012.03.098

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 journal › Article

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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