1992 Fiscal Year Final Research Report Summary
Design of Versatile Chiral Building Blocks via Asymmetric Cleavage of the Bridged Bicyclic Ketone and Its Applications to the Natural Product Synthesis
| Project/Area Number |
03670994
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| Research Category |
Grant-in-Aid for General Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Research Field |
Chemical pharmacy
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| Research Institution | TOYAMA MEDICAL AND PHARMACEUTICAL UNIVERSITY |
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Principal Investigator |
MOMOSE Takefumi TOYAMA MED. & PHARM. UNIVERSITY FACULTY OF PHARMACEUTICAL SCIENCES PROFESSOR, 薬学部, 教授 (50028833)
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| Co-Investigator(Kenkyū-buntansha) |
TOYOOKA Naoki TOYAMA MED. & PHARM. UNIVERSITY FACULTY OF PHARMACEUTICAL SCIENCES RESEARCH ASSO, 薬学部, 助手 (10217565)
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| Project Period (FY) |
1991 – 1992
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| Keywords | bridged bicyclic compound / 'fork head' ketone / (+)-monomorine I / (-)-indolizidine 223AB / sigma-symmetric ring-crossed glycol / functionalized 3-piperidinol |
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| Research Abstract |
We have focused our attention on the bridged bicyclic compound as one of the useful starting material for stereoselective synthesis of natural products because of its conformational rigidity and sigma-symmetry.Thus, in this research project, we have developed the asymmetric synthesis of versatile chiral building blocks for the synthesis of biologically active alkaloids based on the asymmetric cleavage of the nitrogen-bridged bicyclic 'fork head' ketone according to the Koga's protocol to afford cis-2,5-disubstituted pyrrolidine, cis-2,6-disubstituted, and cis-3,5- disubstituted piperidine ring systems.
As a result, we acheived the total synthesis of (+)-dihydropinidine, the dihydro compound of (-)-pinidine, (+)-monomorine I, a trail pheromone of the pharaoh ant, and (-)-indolizidine 223AB.
In addition, we designed a sigma-symmetric ring-crossed glycol and examined its transformation into a homochiral ketone via lipase-catalyzed differentiation of the hydroxyl. The cleavage of the ketone obtained furnished a highly functionalized 3-piperidinol.
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