Natural Product Synthesis by Utilizing Small Ring Hydrocarbons Possessing Hetero Substituents
| Project/Area Number |
15H03806
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| Research Category |
Grant-in-Aid for Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Synthetic chemistry
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| Research Institution | Hokkaido University |
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Principal Investigator |
Tanino Keiji 北海道大学, 理学研究院, 教授 (40217146)
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| Project Period (FY) |
2015-04-01 – 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: ¥5,330,000 (Direct Cost: ¥4,100,000、Indirect Cost: ¥1,230,000)
Fiscal Year 2016: ¥5,330,000 (Direct Cost: ¥4,100,000、Indirect Cost: ¥1,230,000)
Fiscal Year 2015: ¥5,980,000 (Direct Cost: ¥4,600,000、Indirect Cost: ¥1,380,000)
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| Keywords | 小員環 / 開環反応 / 環化反応 / 酸素求核剤 / 合成化学 / 置換反応 / アルキルハライド / アルコール / 有機化学 / 天然物 / 転位反応 |
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| Outline of Final Research Achievements |
New synthetic reactions utilizing small ring hydrocarbons with hetero substituents were developed. A bicyclo[4.2.0]octane derivative was synthesized on the basis of the intramolecular cyclization reaction of a vinyl sulfide possessing a leaving group. A new divinylcyclobutane rearrangement reaction was developed by using 2,2-divinylcyclobutanecarbonitrile as a useful building block. The adduct derived from the four-membered nitrile and a cyclohexanone derivative was treated with an acid, giving rise to a bicyclo[6.4.0]undecane derivative via the Cope rearrangement.
On the other hand, squarate dianion was found to exhibit high reactivity as an oxygen nucleophile, which enabled the transformation of primary and secondary chlorides and bromides to the corresponding alcohols in high yields.
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Report
(4 results)
Research Products
(24 results)
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[Journal Article] Synthesis of yellow and red fluorescent 1,3a,6a-triazapentalenes and the theoretical investigation of their optical properties2015
Author(s)
Kosuke Namba, Ayumi Osawa, Akira Nakayama, Akane Mera, Fumi Tano, Yoshiro Chuman, Eri Sakuda, Tetsuya Taketsugu, Kazuyasu Sakaguchi, Noboru Kitamura, Keiji Tanino
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Journal Title
Chemical Science
Volume: 6
Issue: 2
Pages: 1083-1093
DOI
Related Report
Peer Reviewed / Open Access / Acknowledgement Compliant
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[Journal Article] Novel Inhibitors Targeting PPM1D Phosphatase Potently Suppress Cancer Cell Proliferation.2015
Author(s)
Ogasawara, S., Kiyota, Y., Chuman, Y., Kowata, A., Yoshimura, F., Tanino, K., Kamada, R., and Sakaguchi, K.
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Journal Title
Bioorg. Med. Chem.
Volume: 23
Issue: 19
Pages: 6246-6249
DOI
Related Report
Peer Reviewed / Open Access
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[Journal Article] Total Synthesis of Palau’amine2015
Author(s)
K. Namba, K. Takeuchi, Y. Kaihara, M. Oda, A. Nakayama, A. Nakayama, M. Yoshida, and K. Tanino
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Journal Title
Nature Communications
Volume: 6
Issue: 1
Pages: 8731-8731
DOI
NAID
Related Report
Peer Reviewed / Open Access / Int'l Joint Research / Acknowledgement Compliant
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