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 |
Section | 一般 |
Research Field |
Chemical pharmacy
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Research Institution | Chiba University |
Principal Investigator |
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Project Period (FY) |
2013-04-01 – 2017-03-31
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Project Status |
Completed (Fiscal Year 2016)
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Budget Amount *help |
¥19,110,000 (Direct Cost: ¥14,700,000、Indirect Cost: ¥4,410,000)
Fiscal Year 2016: ¥3,770,000 (Direct Cost: ¥2,900,000、Indirect Cost: ¥870,000)
Fiscal Year 2015: ¥3,770,000 (Direct Cost: ¥2,900,000、Indirect Cost: ¥870,000)
Fiscal Year 2014: ¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2013: ¥7,670,000 (Direct Cost: ¥5,900,000、Indirect Cost: ¥1,770,000)
|
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 / 不斉全合成 / Diels-Alder反応 / カルバゾール / カルバゾマイシン / 全合成 / 構造活性相関研究 / 不斉脱プロトン化反応 / ランドリンB / グランジロジンC / ラピディレクチンB / ミノビンシン / コプシアアルカロイド / ランドリンB / ビニルインドール / 希土類触媒 / ストリキニーネ / スエヒロタケ / 天然物合成 / 悪性黒色腫 / シクロプロパン / 不斉Diels-Alder反応 / ヒドロカルバゾール |
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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Report
(5 results)
Research Products
(48 results)
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[Journal Article] Total synthesis of schizocommunin and revision of its structure2013
Author(s)
Uehata, K., Kimura, N., Hasegawa, K., Arai, S., Nishida, M., Hosoe, T., Kawai, K.-I., Nishida, A.
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Journal Title
Journal of Natural Products
Volume: 76
Issue: 11
Pages: 2034-2039
DOI
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Peer Reviewed
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[Presentation] Total Synthesis of Lundurine A2013
Author(s)
Nakajima, Masaya, Arai, Shigeru, Nishida, Atsushi
Organizer
13th International Conference on the Chemistry of Antibiotics and other bioactive compounds (ICCA-13)
Place of Presentation
山梨
Related Report
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