| Project/Area Number |
10640516
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Organic chemistry
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| Research Institution | Shizuoka University |
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Principal Investigator |
YODA Hidemi Faculty of Engineering, Shizuoka University Associate Professor, 工学部, 助教授 (20201072)
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| Project Period (FY) |
1998 – 1999
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| Project Status |
Completed (Fiscal Year 1999)
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| Budget Amount *help |
¥3,300,000 (Direct Cost: ¥3,300,000)
Fiscal Year 1999: ¥1,100,000 (Direct Cost: ¥1,100,000)
Fiscal Year 1998: ¥2,200,000 (Direct Cost: ¥2,200,000)
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| Keywords | Natural Product / Alkaloid / Lactam / Stereoselective Reduction / Sugar / Amino Acid / Chiral Pool / Chiron / Broussonetine / キラル プール |
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| Research Abstract |
We have recently reported novel and stereoselective methods for the construction of homochiral lactam derivatives elaborated from tartaric acid, sugar, and glutamic acid as a chiral pool, and demonsrtated the possibility for the total synthesis of biologically active alkaloids employing these compouds.
In this conection we wish to communicate two results that a stereoselective route to enantiomerically and diastereomerically pure pentasubstituted pyrrolidines has been developed by using reductive deoxygenation and/or stereoselective reduction of quaternary α-hydroxy N-Boc pyrrolidine derivatives prepared from alkylation of the functionalized homochiral lactams. In the latter case, especially, it could proceed through the predominant attack of HィイD1-ィエD1 on the carbonyl function from the top face of the six-membered metal-chalate rather than five-membered one due to the shielding effect of the three large functional groups.
Finally, an efficient and stereodefined process was described for the first asymmetric synthesis of a tetrasubstituted pyrrolidine alkaloid, broussonetine C, as a potent β-galactosidase and β-mannosidase inhibitor by featuring the elaboration through this stereoselective reduction method.
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