Toward total synthesis of luminamicin, a specific anti-anaerobic bacteriacide and creation of a truncated analog
Project/Area Number |
26860015
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Research Category |
Grant-in-Aid for Young Scientists (B)
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Allocation Type | Multi-year Fund |
Research Field |
Chemical pharmacy
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Research Institution | Kitasato University |
Principal Investigator |
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Project Period (FY) |
2014-04-01 – 2016-03-31
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Project Status |
Completed (Fiscal Year 2015)
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Budget Amount *help |
¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2015: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2014: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
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Keywords | 天然物全合成 / ルミナミシン / マクロライド / 10員環ラクトン / シスデカリン / Juliaカップリング / 1,6-oxa Michael / 抗嫌気性菌活性 / 全合成 / 天然物 / 14員環ラクトン / エノールエーテル / シスデカリン骨格 |
Outline of Final Research Achievements |
Luminamicin was found to exhibit selective antibacterial activity against anaerobic bacteria by our group in 1985. It contains a highly functionalized 11-oxatricycloundecane, associated with a 10-membered lactone moiety which possesses a (E)-trisubstituted olefin and a 14-membered macrolactone, with an enol ether conjugated with a maleic anhydride functionality. Due to its intriguing structure and interesting biological activity, we have been focusing on its total synthesis. Herein, we report the construction of core frameworks; 1) the oxa-bridged cis-decalin ring system bearing a side chain utilizing Michael-aldol reaction and 1,6-oxa-Michael reaction, and 2) the 10-membered lactone using a ring expansion reaction of an acetal through intramolecular Julia coupling.
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Report
(3 results)
Research Products
(7 results)
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[Journal Article] Jietacins with potent nematocidal activity; efficient isolation of novel analogues and divergent total synthesis of jietacin A, B, C, and D2015
Author(s)
4) Akihiro Sugawara, Masahiko Kubo, Takuji Nakashima, Tomoyasu Hirose, Noriaki Tsunoda, Kyoichi Yahagi, Yukihiro Asami, Takeshi Yamada, Kazuro Shiomi, Yoko Takahashi, Satoshi Omura, Toshiaki Sunazuka
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Journal Title
Tetrahedron
Volume: 71
Issue: 14
Pages: 2149-2157
DOI
Related Report
Peer Reviewed
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