Toward the total synthesis of Luminamicin: construction of 14-membered lactone framework possessing versatile enol ether moiety |
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| Authors: | Aoi Kimishima Tomoyasu Hirose Akihiro Sugawara Takanori Matsumaru Kaoru Nakamura Ken Katsuyama Masaki Toda Hirokazu Takada Rokuro Masuma Satoshi Ōmura Toshiaki Sunazuka |
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| Affiliation: | Kitasato Institute for Life Sciences and Graduate School of Infection Control Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan |
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| 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. |
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