2005 Fiscal Year Final Research Report Summary
Synthesis of Jellyfish-Type Macrocyclic Molecular Flask and Efficient Reaction Using the Molecular Flask
| Project/Area Number |
15550039
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Organic chemistry
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| Research Institution | Kumamoto University |
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Principal Investigator |
NISHINO Hiroshi Kumamoto University, Science, Professor, 理学部, 教授 (50145281)
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| Project Period (FY) |
2003 – 2005
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| Keywords | Molecular Flask / Cage-Type macrocyclic Copounds / Intermolecular Radical Cyclization / Intramolecular Radical Cyclization / Manganese(III) Acetate / Oxidative Radical Reaction / Cyclophene-Type Macrodiolides / 1,3-Dicarbonyl Compounds |
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| Research Abstract |
This research project was proposed that an artificial molecular flask such as a cage-type mocrocyclic compound would be synthesized and a highly efficient reaction would be carried out using the molecular flask similar to that using a protein pocket in vivo. The protein pocket in vivo is a three-dimensional hole and it is an efficient reaction flask using hydrogen bond, π-electron interaction, steric repulsion, and so on. Then we planed to synthesize an original cage-type molecular macrocyclic compound using the manganese(III)-based oxidative radical macrocyclization reaction.
We developed the manganese(III)-based oxidative radical macrocyclization reaction and the synthesis of up to dihydrofuran-fused fifty-membered macrocyclic compounds was achieved, This reaction is very efficient and the yield is also high. Therefore, we examined to synthesize the original cage-type molecular macrocyclic compounds using the manganese(III)-based oxidative radical macrocyclization reaction. When the c
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age-type macrocyclic compounds would be synthesized, it would be examined the following items ;
1) the inclusion of a guest organic compound into the cavity of the cage-type macrocyclic compounds,
2) the immobilization of the guest organic compound and reagents in the cavity using the hydrogen bond, π-electron interaction, and/or steric repulsion,
3) the highly efficient reaction of the guest organic compound with reagents in the cavity,
4) the extraction and separation of the products after the reaction,
5) the recovery and reuse of the cage-type macrocyclic compounds.
Although the cage-type macrocyclic compounds were not synthesized, sixty-five-membered cyclophene-type macrocyclic compounds were prepared. In addition, the synthesis of nine- to eighteen-membered microdiolides were achieved. Furthermore, many new guest organic molecules were synthesized.
In the near future, we will plane to investigate the functional ability of the synthesized cyclophene-type macrocyclic compounds. In the event, we will achieve the synthesis of cage-type molecular macrocyclic compounds and investigate the functional ability for the biomimetic molecular flask. Finally, we will develop the highly stereoselective organic reactions using the cage-type molecular macrocyclic compounds. Less
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