2016 Fiscal Year Final Research Report
Synthetic Study of Polycyclic Natural Alkaloids and Application to Drug Development
| Project/Area Number |
25293001
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| Research Category |
Grant-in-Aid for Scientific Research (B)
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| Allocation Type | Partial Multi-year Fund |
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| Section | 一般 |
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| Research Field |
Chemical pharmacy
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| Research Institution | Chiba University |
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Principal Investigator |
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| Project Period (FY) |
2013-04-01 – 2017-03-31
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| Keywords | アルカロイド / ランドリン / グランジロジン / シゾコムニン / イルシナールA / マンザミンA / アレルギー性肺真菌症 / 抗メラノーマ薬 |
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| Outline of Final Research Achievements |
Syntheses of several polycyclic alkaloids have been studied. 1) Structurally unique Kopsia alkaloids, lundurines, which have a cyclopropane-fused indoline skeleton, and grandilodine C have been synthesized firstly. 2) Total synthesis of minovincine was achieved by catalytic asymmetric Diels-Alder reaction of (siloxyvinyl)indole and substituted alkenes using chiral holmium catalyst. A core skeleton of strychnine was prepared by diastereoselective Diels-Alder reaction under catalytic conditions using thulium or scandium salt. 3) Highly efficient total synthesis of scizocommunin has been achieved and its structure was confirmed synthetically. Biological activity of scizocommunin was also studied and it showed moderate antiproliferative activity. 3) A manzamine alkaloid, ircinal A has been synthesized in optically active form using furane-iminiumu cation cyclization (FIC). Formal total synthesis of manzamine A has been accomplished.
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| Free Research Field |
医歯薬学
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