Application of the Diastereoselective Ketal Formation Reactions for the Organic Synthesis.
| Project/Area Number |
15K07872
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Multi-year Fund |
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| Section | 一般 |
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| Research Field |
Chemical pharmacy
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| Research Institution | Musashino University |
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Principal Investigator |
HIROYA Kou 武蔵野大学, 薬学研究所, 教授 (70192721)
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| Research Collaborator |
Takahashi Erina
Nakamura Ayumi
Fukuda Chiaki
Hayakawa Emi
Watanabe Akiho
Ohkubo Mami
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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 |
¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000)
Fiscal Year 2017: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2016: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2015: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
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| Keywords | ジアステレオ選択的反応 / ケタール化反応 / 不斉第四級炭素 / 不斉四置換炭素 / 不斉合成 / 生物活性 / アルカロイド / 不斉ジヒドロキシル化反応 |
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| Outline of Final Research Achievements |
The expansion of the substrates for the diastereoselective ketal formation reaction have been established as my primary object. The products of the diastereoselective ketal formation seem to be useful for synthetic organic chemistry. Therefore, I have arranged the synthesis of the important compounds as an optically active form for my second object.
Firstly, compounds having an aromatic ring and cinnamyl unit at C2 position of 1,3-cyclohexanedione have been synthesized and highly diastereoselective hemiketal and intermolecular ketal formation reaction have been achieved. Next, the asymmetric dihydroxylation reaction was examined utilizing commercially available reagents. As a result, the products which have almost 90%e.e. were afforded. Secondly, the conversion of the quaternary carbon center to chiral four substituted center was investigated and single lactam was obtained by Beckmann rearrangement. Synthetic studies of two natural products as optically active forms are now under way.
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Report
(4 results)
Research Products
(15 results)
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[Journal Article] Catalytic Synthesis of Saturated Oxygen Heterocycles by Hydrofunctionalization of Unactivated Olefins: Unprotected and Protected Strategies2016
Author(s)
Hiroki Shigehisa, Miki Hayashi, Haruna Ohkawa, Tsuyoshi Suzuki, Hiroki Okayasu, Mayumi Mukai, Ayaka Yamazaki, Ryohei Kawai, Harue Kikuchi, Yui Satoh, Akane Fukuyama, Kou Hiroya
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Journal Title
Journal of the American Chemical Society
Volume: 138
Issue: 33
Pages: 10597-10604
DOI
Related Report
Peer Reviewed / Acknowledgement Compliant
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