2022 Fiscal Year Annual Research Report
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 Institution | Microbial Chemistry Research Foundation |
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Principal Investigator |
崔 進 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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| Keywords | vinylogous addition / chromone / enolates / total synthesis / natural product |
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| Outline of Annual Research Achievements |
This study provided new methods to access chiral chromanone lactones with potential biological activities. The developed approach involves copper-catalyzed asymmetric vinylogous addition of siloxyfurans or butenolide to chromones. By using chiral ligands, the diastereo- and enantioselective addition of copper vinylogous enolate to chromones can be controlled with high regio- and stereoselectivity. These approaches were used for the synthesis of various chromanone lactones and applied in the total synthesis of ent-blennolide B. Additionally, secalonic acid A was synthesized formally using ent-blennolide B as an intermediate.
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| Remarks |
微生物化学研究所 https://www.bikaken.or.jp/
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