Synthetic Study of Biologically Active Natural Products Based on the Novel Chiral Pool Approach
Project/Area Number |
26288018
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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 |
Organic chemistry
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Research Institution | Keio University |
Principal Investigator |
CHIDA Noritaka 慶應義塾大学, 理工学部(矢上), 教授 (50197612)
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Project Period (FY) |
2014-04-01 – 2018-03-31
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Project Status |
Completed (Fiscal Year 2017)
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Budget Amount *help |
¥16,640,000 (Direct Cost: ¥12,800,000、Indirect Cost: ¥3,840,000)
Fiscal Year 2017: ¥3,380,000 (Direct Cost: ¥2,600,000、Indirect Cost: ¥780,000)
Fiscal Year 2016: ¥3,380,000 (Direct Cost: ¥2,600,000、Indirect Cost: ¥780,000)
Fiscal Year 2015: ¥3,380,000 (Direct Cost: ¥2,600,000、Indirect Cost: ¥780,000)
Fiscal Year 2014: ¥6,500,000 (Direct Cost: ¥5,000,000、Indirect Cost: ¥1,500,000)
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Keywords | 天然物合成 / キラルプール法 / タキソール / ネオステニン / カイトセファリン / 有機合成化学 / ステニン / パクリタキセル / 全合成 |
Outline of Final Research Achievements |
The chiral pool approach is a highly effective and reliable method for the synthesis of biologically active natural products in optically pure form. In this project, synthetic studies toward taxol (diterpenoids possessing anticancer activity), neostenine (alkaloid with antitussive activity), and kaitocephalin (amino acid with antagonistic activity of glutamate receptor), based on the chiral pool approach utilizing carbohydrate as starting material, were carried out. The successful syntheses of these natural products revealed the effectiveness of the chiral pool methodology and brought about the progress of the methodology.
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Report
(5 results)
Research Products
(60 results)
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[Journal Article] Crystal structure of (+/-)-(1SR,5SR,6SR,7SR,10SR,11SR,13SR)-14-benzoyloxy-7-methodymethoxy-11,15,18,18-tetramethyl-3-oxo-2,4-dioxatetracyclo[12.3.1.0.0]octadeca-14,16-dien-10-yl benzoate2015
Author(s)
T. Oishi, K. Fukaya, Y. Yamaguchi, T. Sugai, A. Watanabe, T. Sato and N. Chida
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Journal Title
Acta Crystallographica Section E
Volume: 71
Issue: 5
Pages: 490-493
DOI
Related Report
Peer Reviewed / Open Access
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[Journal Article] Synthesis of Paclitaxel. 1. Synthesis of the ABC-Ring of Paclitaxel by SmI2-Mediated Cyclization2015
Author(s)
Fukaya, K.; Tanaka, Y.; Sato, A.; Kodama, K.; Yamazaki, H.; Ishimoto, T.; Nozaki, Y.; Iwaki, Y.; Yuki, Y.; Umei, K.; Sugai, T.; Yamaguchi, Y.; Watanabe, A.; Oishi, T.; Sato, T.; *Chida, N.
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Journal Title
Organic Letters
Volume: 17
Issue: 11
Pages: 2570-2573
DOI
Related Report
Peer Reviewed / Int'l Joint Research
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[Journal Article] Synthesis of Paclitaxel. 2. Construction of the ABCD-Ring and Formal Synthesis2015
Author(s)
Fukaya, K.; Kodama, K.; Tanaka, Y.; Yamazaki, H.; Sugai, T.; Yamaguchi, Y.; Watanabe, A.; Oishi, T.; *Sato, T.; *Chida, N.
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Journal Title
Organic Letters
Volume: 17
Issue: 11
Pages: 2574-2577
DOI
Related Report
Peer Reviewed / Int'l Joint Research
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[Journal Article] Crystal structure of (+/-)-(4RS,5RS,7SR)-4-[(1RS,2RS,3RS,6RS)-3-benzoyloxy-2-(2-hydroxyethyl)-6-methoxymethoxy-2-methylcyclohexyl]-8,10,10-trimethyl-2-oxo-1,3-dioxaspiro[4.5]dec-8-en-7-yl benzoate benzene monosolvate2015
Author(s)
T. Oishi, Y. Yamaguchi, K. Fukaya, T. Sugai, A. Watanabe, T. Sato, and N. Chida
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Journal Title
Acta Crystallographica Section E
Volume: 71
Issue: 1
Pages: 8-11
DOI
Related Report
Peer Reviewed / Open Access
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[Journal Article] Crystal structures of (±)-(1SR,5SR,6SR,7SR,10SR,11SR,13RS,14SR)-13-hydroxy-7-methoxymethoxy-11,15,18,18-tetramethyl-3-oxo-2,4-dioxatetracyclo[12.3.1.0-1,5.0-6,11]octadec-15-en-10-yl benzoate, its 13-epimer and 13-one derivative2015
Author(s)
T. Oishi, K. Fukaya, Y. Yamaguchi, T. Sugai, A. Watanabe, T. Sato, and N. Chida
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Journal Title
Acta Crystallographica Section E
Volume: 71
Issue: 5
Pages: 466-472
DOI
Related Report
Peer Reviewed / Open Access
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[Presentation] (-)-ゼフィランチンの全合成2017
Author(s)
石井孝樹,石橋瑞基,関結菜,佐藤隆章,千田憲孝
Organizer
日本化学会第97春季年会
Place of Presentation
慶應義塾大学日吉キャンパス(横浜市港北区)
Year and Date
2017-03-16
Related Report
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[Presentation] タキソールの改良合成研究2017
Author(s)
渡部愛海,深谷圭介,山本拓央,佐藤隆章,千田憲孝
Organizer
日本化学会第97春季年会
Place of Presentation
慶應義塾大学日吉キャンパス(横浜市港北区)
Year and Date
2017-03-16
Related Report
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[Presentation] タキソールの合成研究2016
Author(s)
千田憲孝
Organizer
第71回有機合成化学協会関東支部シンポジウム
Place of Presentation
東京農工大学小金井キャンパス(東京都小金井市)
Year and Date
2016-05-14
Related Report
Invited
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[Presentation] タキソールの合成研究2016
Author(s)
千田憲孝
Organizer
有機化学研究会第76回講演会(白鷺セミナー)
Place of Presentation
大阪府立大学(大阪府堺市)
Year and Date
2016-04-08
Related Report
Invited
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[Presentation] Synthesis of Taxol2015
Author(s)
K. Fukaya, T. Sugai, H. Yamazaki, K. Kodama, T. Sato, and N. Chida
Organizer
The 13th International Conference on New Aspects of Organic Chemistry
Place of Presentation
Rihga Royal Hotel Kyoto (Kyoto, Japan)
Year and Date
2015-11-09
Related Report
Int'l Joint Research
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[Presentation] リコリン類の合成研究2015
Author(s)
関結菜、石橋瑞基、佐藤隆章、千田憲孝
Organizer
日本化学会第95春季年会
Place of Presentation
日本大学理工学部船橋キャンパス(千葉県・船橋市)
Year and Date
2015-03-26 – 2015-03-29
Related Report
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[Presentation] Synthesis of Taxol2015
Author(s)
K. Fukaya, T. Sugai, H. Yamazaki, K. Kodama, Y. Yamaguchi, T. Sato, and N. Chida
Organizer
日本化学会第95春季年会
Place of Presentation
日本大学理工学部船橋キャンパス(千葉県・船橋市)
Year and Date
2015-03-26 – 2015-03-29
Related Report
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[Book] アルカロイドの科学2017
Author(s)
高山 廣光(編),千田 憲孝(分担執筆)
Total Pages
560
Publisher
化学同人
ISBN
9784759814187
Related Report
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