The Development of Direct Vinylogous Michael Addition of Butenolides to Chromones and Its Application to the Total Synthesis of Natural Products
| Project/Area Number |
20K15966
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| Research Category |
Grant-in-Aid for Early-Career Scientists
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| Allocation Type | Multi-year Fund |
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| Review Section |
Basic Section 47010:Pharmaceutical chemistry and drug development sciences-related
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| Research Institution | Microbial Chemistry Research Foundation |
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Principal Investigator |
Cui Jin 公益財団法人微生物化学研究会, 微生物化学研究所, 研究員 (20839120)
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| Project Period (FY) |
2020-04-01 – 2023-03-31
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| Project Status |
Completed (Fiscal Year 2022)
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| Budget Amount *help |
¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2022: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2021: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2020: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
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| Keywords | total synthesis / asymmetric catalysis / enolate / copper / vinylogous addition / chromone / enolates / natural product / atom-economy / chromanone lactones / catalytic synthesis / butenolides / natural products |
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| Outline of Research at the Start |
In this project, a novel catalytic asymmetric synthetic method for the chromone lactone compounds will be established. The intriguing enantioface-differentiation mechanism for the unexpected and unprecedented anti-selectivity will be clarified. (+)-Lachnone C, epi-(+)-microdiplodiasone, (+)-gonytolides C&G and their simplified analogues will be synthesized and subjected to in vitro screening in order to identify the potential antibacterial and/or anticancer lead compounds
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| Outline of Final Research Achievements |
This study achieved the development of a new synthetic method for chromanone lactones. The method is applicable to chromones with different substitution groups and has yielded natural product analogs with excellent diastereo- and enantioselectivity. Additionally, successful syntheses of ent-blennolide B and secalonic acid A were also achieved.
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| Academic Significance and Societal Importance of the Research Achievements |
The method developed in this study could be used for the synthesis of biologically important natural products in an effective manner which may accelerate drug discovery based on natural products.
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Report
(4 results)
Research Products
(10 results)
