2006 Fiscal Year Final Research Report Summary
Development of new transforming reaction using New Mitsunobu reaction and deracemization
| Project/Area Number |
17590026
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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 |
Chemical pharmacy
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| Research Institution | Tokushima Bunri University |
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Principal Investigator |
TSUNODA Tetsuto Tokushima Bunri University, Pharmaceutical Sciences, Professor, 薬学部, 教授 (00172049)
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| Co-Investigator(Kenkyū-buntansha) |
NISHII Takeshi Tokushima Bunri University, Pharmaceutical Sciences, Research Associate, 薬学部, 助手 (40341268)
HORIKAWA Mitsuyo Tokushima Bunri University, Pharmaceutical Sciences, Research Associate, 薬学部, 助手 (50148772)
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| Project Period (FY) |
2005 – 2006
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| Keywords | Mitsunobu Reaction / Dios group / antimycin / asymmetric reaction / aza-Claisen rearrangement / aldol reaction / pigment / aphid |
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| Research Abstract |
2-(1,3-Dioxa-2-yl)ethylsulfonyl (Dios) chloride was synthesized and used as a new versatile sulfonating agent for amines. Primary and secondary amines were sulfonated very easily in excellent yields with Dios chloride. N-nonsubstituted and N-monosubstituted Dios-amides, activated amines, were alkylated satisfactorily under new Mitsunobu conditions utilizing (cyanomethylene) tributylphosphorane (CMBP). The Dios group was very stable under basic and reductive conditions and was removed by heating in a hot aqueous solution of trifluoroacetic acid.
The antimycin A (AA) family isolated from Streptomyces sp. possesses significant biological activities, such as antifungal, insecticidal, and anticancer, as well as an inhibitory activity against ubiquinol-cytochrome c oxidoreductase. We performed the first and efficient synthesis of (+)-AA_9, which is the first antimycin having an aromatic 8-acyl residue.
Uroleuconaphins A1 and B1 are red pigments isolated from Uroleucon nigrotuberculatum O., and their structures were determined by a single crystal X-ray analysis of them.
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