1999 Fiscal Year Final Research Report Summary
Novel Methods for the construction of Biologically Active Natural Products based on a chiron-synthetic strategy
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 |
Section | 一般 |
Research Field |
Organic chemistry
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Research Institution | Shizuoka University |
Principal Investigator |
YODA Hidemi Faculty of Engineering, Shizuoka University Associate Professor, 工学部, 助教授 (20201072)
|
Project Period (FY) |
1998 – 1999
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Keywords | Natural Product / Alkaloid / Lactam / Stereoselective Reduction / Sugar / Amino Acid / Chiral Pool / Chiron |
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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