Development of the stereocontrolled synthesis of the highly oxygenated steroids
Project/Area Number |
25460007
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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 | The University of Tokyo |
Principal Investigator |
Urabe Daisuke 東京大学, 薬学研究科(研究院), 講師 (80503515)
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Project Period (FY) |
2013-04-01 – 2016-03-31
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Project Status |
Completed (Fiscal Year 2015)
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Budget Amount *help |
¥5,200,000 (Direct Cost: ¥4,000,000、Indirect Cost: ¥1,200,000)
Fiscal Year 2015: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2014: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Fiscal Year 2013: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
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Keywords | 有機合成化学 / 天然物 / 生物活性物質 / 全合成 / 立体選択性 / ステロイド / 立体化学 / 立体選択的変換反応 / アルドール反応 / グリコシル化 / 生理活性物質 / ラジカル反応 / カップリング |
Outline of Final Research Achievements |
In this research project, we have established the strategy for the divergent synthesis of the highly oxygenated steroid compounds. The stereocontrolled synthesis of the core system of the steroid has been developed by the convergent radical coupling of the diverse AB-rings and the D-ring and the following stereoselective intramolecular aldol reaction. Based on the developed method, the total synthesis of complex natural product ouabagenin has been achieved. Furthermore, the intermediate towards toosendanine has been synthesized.
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Report
(4 results)
Research Products
(74 results)
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[Journal Article] Total synthesis of four stereoisomers of (5Z,8Z,10E,14Z)-12-hydroxy-17,18-epoxy-5,8,10,14-eicosatetraenoic acid and their anti-Inflammatory activities2015
Author(s)
Goto, T.; Urabe, D.; Isobe, Y.; Arita, M.; Inoue, M.
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Journal Title
Tetrahedron
Volume: 71
Issue: 43
Pages: 8320-8332
DOI
Related Report
Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
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[Journal Article] Total synthesis of four stereoisomers of (4Z,7Z,10Z,12E,16Z,18E)-14,20-dihydroxy-4,7,10,12,16,18-docosahexaenoic acid and their anti-inflammatory activities.2015
Author(s)
Goto T, Urabe D, Masuda K, Isobe Y, Arita M, Inoue M.
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Journal Title
J Org Chem
Volume: 80
Issue: 15
Pages: 7713-7726
DOI
Related Report
Peer Reviewed / Open Access / Int'l Joint Research
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[Journal Article] Total Synthesis of Ryanodol2014
Author(s)
Masanori Nagatomo, Masaki Koshimizu, Kengo Masuda, Toshiki Tabuchi, Daisuke Urabe, Masayuki Inoue
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Journal Title
Journal of the American Chemical Society
Volume: 136
Issue: 16
Pages: 5916-5919
DOI
Related Report
Peer Reviewed
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[Presentation] タラチサミンの合成研究2016
Author(s)
鎌倉大貴、轟木秀憲、占部大介、井上将行
Organizer
日本薬学会 第136年会
Place of Presentation
パシフィコ横浜、横浜
Year and Date
2016-03-26
Related Report
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[Presentation] プベルリンCの全合成研究2015
Author(s)
萩原浩一、田渕俊樹、占部大介、井上将行
Organizer
第13回次世代を担う有機化学シンポジウム
Place of Presentation
立命館大学、大津
Year and Date
2015-05-22
Related Report
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[Presentation] プベルリンCの合成研究2015
Author(s)
萩原浩一、田渕俊樹、占部大介、井上将行
Organizer
日本薬学会第135年会
Place of Presentation
兵庫
Year and Date
2015-03-25 – 2015-03-28
Related Report
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[Presentation] タラチサミンの全合成研究2015
Author(s)
轟木秀憲、鎌倉大貴、占部大介、井上将行
Organizer
日本薬学会第135年会
Place of Presentation
兵庫
Year and Date
2015-03-25 – 2015-03-28
Related Report
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[Presentation] Total synthesis of crotophorbolone2014
Author(s)
Taro Asaba, Yuki Katoh, Daisuke Urabe, Masayuki Inoue
Organizer
JICCEOCA-4 and ICCEOCA-9/NICCEOCA-5
Place of Presentation
bangkok, thailand/Kuala Lumpur, Malaysia
Year and Date
2014-11-25 – 2014-12-08
Related Report
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[Presentation] クロトホルボロンの全合成2014
Author(s)
浅羽太郎、嘉藤裕樹、占部大介、井上将行
Organizer
第40回反応と合成の進歩シンポジウム
Place of Presentation
宮城
Year and Date
2014-11-10 – 2014-11-11
Related Report
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[Presentation] プベルリンCの合成研究2014
Author(s)
萩原浩一、田渕俊樹、占部大介、井上将行
Organizer
第105回有機合成シンポジウム
Place of Presentation
東京
Year and Date
2014-06-10 – 2014-06-11
Related Report
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[Presentation] Synthetic study of 4-hydroxyzinowol2013
Author(s)
Todoroki, H.; Iwatsu, M.; Masuda, K.; Urabe, D.; Inoue, M.
Organizer
The 8th International Conference on Cutting-Edge Organic Chemistry in Asia and The 4th New Phase International Conference on Cutting-Edge Organic Chemistry in Asia
Place of Presentation
大阪府、大阪市
Related Report
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