2023 Fiscal Year Final Research Report
Stereoselective synthesis of polysubstituted unsaturated carbocyclic compounds via a novel domino reaction
Project/Area Number |
21K05411
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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 |
Review Section |
Basic Section 38040:Bioorganic chemistry-related
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Research Institution | Gifu University |
Principal Investigator |
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Project Period (FY) |
2021-04-01 – 2024-03-31
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Keywords | ドミノ反応 / Julia-Kocienskiスルホン / シクロペンテン / シクロヘキセン / 炭素環ヌクレオシド / ヌクレオシド |
Outline of Final Research Achievements |
We have discovered that nucleoside-derived Julia-Kocienski sulfones afford cyclopentene derivatives via a domino reaction upon treatment with a base. Nucleophiles can be incorporated into the cyclopentene core in this domino reaction. In this study, we explored the applicability of this novel domino reaction to the Julia-Kocienski sulfones derived from 5- and 6-membered sugars. First, we attempted the reaction of sulfones derived from D-ribose with nucleobases and found that the corresponding cyclopentene derivatives could be obtained from various nucleobases. We also achieved the synthesis of Julia-Kocienski sulfones from various aldopentoses, hexoses, and ketoses, and found that cyclopentene and cyclohexene derivatives can be generated by the same domino reaction.
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Free Research Field |
有機化学、生体関連化学
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Academic Significance and Societal Importance of the Research Achievements |
本研究で開発した手法は、光学活性シクロペンテン、シクロヘキセンの効率的な合成法として有用である。特に、加えた求核剤が高立体選択的にシクロペンテン、シクロヘキセン環へと導入されるため、一つの原料から多彩な化合物が得られることが特徴である。得られる光学活性シクロペンテン、シクロヘキセンは、様々な生物活性物質などの合成中間体としての応用が期待される。中でも、様々な核酸塩基から合成される炭素環ヌクレオシドは、抗ウイルス薬への応用が期待できる。
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