2015 Fiscal Year Final Research Report
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 |
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| Research Field |
Chemical pharmacy
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| Research Institution | Kitasato University |
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Principal Investigator |
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| Project Period (FY) |
2014-04-01 – 2016-03-31
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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 |
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| 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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| Free Research Field |
有機合成化学
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