1991 Fiscal Year Final Research Report Summary
Studies on Design and Synthesis of Biologically Active Natural Products Based on Allenyl Ether Intramolecular Cycloaddition Reaction
| Project/Area Number |
02453143
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| Research Category |
Grant-in-Aid for General Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Research Field |
Chemical pharmacy
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| Research Institution | Kyushu University |
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Principal Investigator |
KANEMATSU Ken Kyushu University Pharmaceutical Sciences Professor, 薬学部, 教授 (70023041)
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| Co-Investigator(Kenkyū-buntansha) |
NAGASHIMA Shigeru Kyushu University Pharmaceutical Sciences Assistant, 薬学部, 助手 (90228007)
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| Project Period (FY) |
1990 – 1991
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| Keywords | Intramolecular Cycloaddition / Allenyl Ether / Total Synthesis / Forskolin / Euryfuran / Furan Ring Transfer Reaction / Lactone / Furan |
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| Research Abstract |
Based on the results of our fundamental research on intramolecular cycloaddition reactions of allenyl ethers, we developed a new method of lactone synthesis via intramolecular Diels-Alder reaction of allenyl ethers followed by hydration and oxidation of the adducts. Applying this strategy, we developed a new synthetic route of an optically active forskolin intermediate.
Moreover, we developed a new method for the transformation of 2-substituted furans to 3, 4-fused furans via the intramolecular Diels-Alder reaction of allenyl furfury ethers followed by base catalyzed ring opening of the resulting adducts (Furan Ring Transfer reaction : FRT reaction). We achieved a total synthesis of euryfuran via two sequential furan ring transfer reaction.
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