2014 Fiscal Year Final Research Report
Development of the synthetic method for natural compound based on the intramolecular aldol reaction
Project/Area Number |
24590023
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Research Category |
Grant-in-Aid for Scientific Research (C)
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Allocation Type | Multi-year Fund |
Section | 一般 |
Research Field |
Chemical pharmacy
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Research Institution | Tokyo University of Pharmacy and Life Science |
Principal Investigator |
HISANAKA Ito 東京薬科大学, 生命科学部, 教授 (70287457)
|
Project Period (FY) |
2012-04-01 – 2015-03-31
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Keywords | 全合成 / 生理活性物質 / 天然有機化合物 / 不斉合成 / 分子内アルドール反応 |
Outline of Final Research Achievements |
Bioactive polyfunctionalized cyclic terpenoid has much attention on developing of medicine. Synthetic study of terpenoid which having complex carbon skeleton is very important for clarify the structure-activity relationship. Synthetic study of two terpenoids, albaflavenone and aberrarone, which having complex and interesting carbon skeleton, was examined. Total synthesis of albaflavenone, antibiotic sesquiterpene, has been accomplished via the concise construction of skeleton utilizing sequential intramolecular aldol condensation. This synthetic work was completed in nine steps without the use of protecting groups and with high stereocontrol. Highly stereocontrolled synthesis of the tetracyclic core of diterpenoid aberrarone, which possesses antimalarial activity, has also been accomplished. A key feature of the synthesis is the complete stereocontrolled construction of C- and D-ring using stereoselective 1,4-addition followed by intramolecular aldol reaction.
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Free Research Field |
有機合成化学
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