1985 Fiscal Year Final Research Report Summary
Highly Stereoselective Synthesis of Biologically Active Conjugated Polyene Compounds
| Project/Area Number |
59850144
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| Research Category |
Grant-in-Aid for Developmental Scientific Research
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| Allocation Type | Single-year Grants |
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| Research Field |
Synthetic chemistry
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| Research Institution | Okayama University |
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Principal Investigator |
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| Project Period (FY) |
1984 – 1985
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| Keywords | polyenoic acid / highly stereoselective synthesis / self defensive substance against rice blast disease / 殺虫剤 |
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| Research Abstract |
1. Synthesis of self defensive substances in rice plant against rice blast disease. Protection of rice blast disease is one of important projects in Japan. In 1984, we could synthesize the methyl ester of dimorphecolic acid (1), the self defensive substance in rice plant against rice blast disease, and its analogs. In 1985, the synthesis of tert-butyl coriolate and tert-butyl (9E,11E,15Z)-13hydroxy-9,11,15-octadecatrienoate was established. These compounds showed no biological activity against rice blast disease. It seems that the esters should be converted to carboxylic acid for the manifestation of biological activity.
2. Although the attempts to synthesize termite trail-following pheromone, (3Z,6Z,8E)-3,6,8-dodecatrien-1-01 resulted in failure, we found a new and novel synthetic method of 2,5-disubstituted furans and selenophenes via oxidation of 2,4-alkadienoic ester with selenium dioxide at the reflux temperature of benzene. It is very interesting because synthesis of furans from dienes under such a mild condition has never been reported.
3. Synthesis of octadecapolyenoic acid. Insecticidal test of compounds prepared in section (1) to drosophilae showed weak effectiveness, but it is not efficient practically.
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