Highly Stereoselective Synthesis of Biologically Active Conjugated Polyene Compounds

生物活性共轭多烯化合物的高度立体选择性合成

• 批准号: 59850144
• 负责人: TAKEDA Akira
• 金额: $ 5.18万
• 依托单位: Okayama University
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Developmental Scientific Research
• 财政年份: 1984
• 资助国家: 日本
• 起止时间: 1984 至 1985
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/en/grant/KAKENHI-PROJECT-59850144/
• 关键词: polyenoic acid; highly stereoselective synthesis; self defensive substance against rice blast disease; 殺虫剤

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.

1。水稻植物中自防御性物质的合成。保护大米爆炸是日本重要项目之一。 1984年，我们可以合成二酚酸的甲基酯（1），水稻植物中针对水稻爆炸疾病的自我防御性物质及其类似物。 1985年，建立了Tert丁基科里奥尔酸盐和丁基（9e，11e，15z）-13 Hydroxy-9,11,15-Octadecatrienoate的合成。这些化合物没有针对水稻爆炸疾病的生物学活性。似乎应将酯转化为羧酸以表现出生物学活性。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.这很有趣，因为在这种温和的情况下从未报道过在这种温和条件下的Furans的合成。3。八核酸酸的合成。在第（1）节为果蝇中制备的化合物的杀虫测试表现出较弱的有效性，但实际上并非有效。

项目成果

Bull.Chem.Soc.Jpn.59-6or7. (1986)

Bull.Chem.Soc.Jpn.59-6or7。

Abstracts of 30th Congress of IUPAC. (1985)

IUPAC 第 30 届大会摘要。

日本化学会第50春季年会講演要旨集. 【II】-866. (1985)

日本化学会第 50 届春季年会摘要 [II]-866 (1985)。

第3回有機合成指向有機金属化学国際会議. 【II】-02. (1985)

第三届有机金属化学国际会议[II]-02（1985）。

第30回国際純正応用化学連合総会要旨集. (1985)

第30届国际纯粹与应用化学联合会大会摘要（1985年）。