Studies on the synthesis of marine alkaloid spirolide D
| Project/Area Number |
26860014
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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 | Nagoya City University |
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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: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2014: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
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| Keywords | スピロリド類 / ジスピロケタール / アルカロイド / 渡環型反応 / テザー / 双極子モーメント / モレキュラーシーブ |
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| Outline of Final Research Achievements |
Toward the total synthesis of marine toxin spirolide D, the stereoselective construction of BCD fragment has been explored. Transannular spiroketalization of the triketone with a tether between the carboxyl group at C10 and hydroxyl group at C24 proceeded stereoselectively to give the desired stereoisomer in good yield. Since the reaction using acyclic triketone gave desired stereoisomer as the major product, the stereoselectivity of this process is rationalized by a preferred dipole orientation. The product was successfully converted to the BCD ring fragment through a stereoselective hydrogenation of C11-C12 double bond.
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Report
(3 results)
Research Products
(7 results)
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[Presentation] Studies on the synthesis of spirolide D2015
Author(s)
Akinori Toita, Keisuke Takeda, ○Hiroyuki Yamakoshi, Seiichi Nakamura
Organizer
2015 International Chemical Congress of Pacific Basin Societies (PACIFICHEM)
Place of Presentation
米国ハワイ州ホノルル市
Year and Date
2015-12-15
Related Report
Int'l Joint Research
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