Development of Enantioselective Acylation Based on Hydrogen-Bonding Strategy
| Project/Area Number |
17K17903
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| Research Category |
Grant-in-Aid for Young Scientists (B)
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| Allocation Type | Multi-year Fund |
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| Research Field |
Synthetic chemistry
Organic chemistry
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| Research Institution | Okayama University |
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Principal Investigator |
Mandai Hiroki 岡山大学, 自然科学研究科, 特任助教 (60534427)
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| Project Period (FY) |
2017-04-01 – 2019-03-31
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| Project Status |
Completed (Fiscal Year 2018)
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| Budget Amount *help |
¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2018: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2017: ¥3,120,000 (Direct Cost: ¥2,400,000、Indirect Cost: ¥720,000)
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| Keywords | 有機分子触媒 / 求核触媒 / アシル化 / エナンチオ選択的 / N,N-ジメチル-4-アミノピリジン / 1,3-ジオール / 糖 / 不斉求核触媒 / エナンチオ選択的アシル化 / 位置選択的アシル化 / グリセロール / ポリオール / DMAP / 速度論的光学分割 / 光学活性化合物 / 不斉触媒反応 |
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| Outline of Final Research Achievements |
With an optically active DMAP with tertiary alcohols moiety developed by our group, we examined enantioselective acylation of more complexed polyols. When the reaction was carried out using linear or cyclic 1,3-diol or 1,2,3-triol derivatives, the target monoacylated products were successfully obtained in high yield with high enantioselectivity. We also examined the regioselective acylation of carbohydrates for the synthesis of chiral building with high synthetic utility value. As a result of various control experiments, it was revealed that this reaction had high reaction acceleration effect and enantioselectivity (or regioselectivity) by hydrogen bonding.
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| Academic Significance and Societal Importance of the Research Achievements |
本研究成果は，医薬品，農薬，天然物などの生物活性化合物合成に利用できるキラルビルディングを迅速かつ効率的に合成できる方法であり，医薬品や農薬などのファインケミカルの分野に大きく波及するものと期待している．
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Report
(3 results)
Research Products
(31 results)
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[Journal Article] Fungal metabolite (+)-terrein suppresses IL-6/sIL-6R-induced CSF1 secretion by inhibiting JAK1 phosphorylation in human gingival fibroblasts2018
Author(s)
Satoshi Yamamoto, Kazuhiro Omori, Hiroki Mandai, Masaaki Nakayama, Saki Nakagawa, Hiroya Kobayashi, Tadashi Kunimine, Hiroshi Yoshimura, Kyosuke Sakaida, Hidefumi Sako, Soichiro Ibaragi, Tadashi Yamamoto, Hiroshi Maeda, Seiji Suga, and Shogo Takashiba
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Journal Title
Heliyon
Volume: 4
Issue: 11
Pages: e00979-e00979
DOI
Related Report
Peer Reviewed / Open Access
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