著者

鈴鴨 剛夫

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.40, no.10, pp.930-938, 1982 (Released:2010-01-22)

参考文献数

42

被引用文献数

6 7

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Chrysanthemic acid (2, 2-dimethyl-3- (2-methyl-1-propenyl) cyclopropanecarboxylic acd) is an acid component of pyrethroidal insecticides. There exist four optical isomers originated from two asymmetric carbon atoms at the C-1 and C-3 positions.Insecticidal activities of the synthetic pyrethroids derived from these optical isomers are shown as follows : 1 R-trans≥1 R-cis>>1 S-trans1 S-cis.Optical resolution of racemic mixture of chrysanthemic acid conveniently gives each isomer in optically pure from.Highly efficient epimerization at the position of C-1, C-3 and racemization were achieved as the method for the conversion of ineffective isomers into effective ones.Secondly, the relationship between stereochemical interconversion and regioselective ring opening of chrysanthemic acid derivatives was investigated. Some of the ring opening products were successfully converted into optically active form of tetrahydrolavandulol and tetralin musks.