M. Matsui, H. Yoshioka, Hideo Sakamoto
1967
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Journal
Agricultural and biological chemistry
Abstract
Pure (+)-trans-chrysanthemic acid was synthesized from (+)-⊿3-carene.Ozonolysis of (+)-⊿3-carene affords 2,2-dimethyl-3-(2-oxo-propyl)-cyclopropyl-acetaldehyde which was cyclized to (+)-2-acety1-6,6-dimethyl-bicyclo-[3,1,0]-2-hexene. The bicyclo compound was transformed into (+)-cis-homocaronic acid by ozonolysis followed by oxidation. Diester or anhydride of the acid and methyl magnesium iodide gave (-)-dihydrochrysanthemolactone which afforded finally (+)-trans-chrysanthemic acid via ethyl (-)cis-chrysanthemate.