2002 Fiscal Year Final Research Report Summary
Synthetic Studies of Bioactive Marine Alkaloids Based on Nitroso-Ene Reaction
| Project/Area Number |
13672232
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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 |
Chemical pharmacy
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| Research Institution | Tokyo University of Pharmacy & Life Science |
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Principal Investigator |
AOYAGI Sakae Tokyo University of Pharmacy & Life Science School of Pharmacy, associate professor, 薬学部, 助教授 (30212385)
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| Project Period (FY) |
2001 – 2002
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| Keywords | marine alkaloids / halichlorine / pinnaic acid / acylnitroso compounds / ene reaction |
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| Research Abstract |
Halichlorine and pinnaic acid are novel marine natural products isolated from the marine sponge and the Okinawan bivalve, respectively. Halichlorine is shown to inhibit the induction of VCAM-1 (vascular cell adhension molecule-1), a potent target for the treatment and coronary heart disease. Pinnaic acid is an inhibitor of phospholipase A2 that has potential for treatment of inflammatory disease. The investigator has developed the synthesis of the spirocyclic core of halichlorine and pinnaic acid. The key steps in the synthetic approach are the preparation of the unique azaspiro[4.5]decan skeleton through the application of the intramolecular enereacton of the N-acylnitroso compound, stereoselective introduction of the tert-butyldimethylsilyloxy)ethyl moiety to the 7-position of the azaspiro[4.5]decan skeleton through a stereoselective introduction of the ethynyl group, and construction of the 2-hydroxy-1-methylethyl moiety onto the 1-position
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