I. Nakatsuka, F. Shono, A. Yoshitake
1977
Citations
0
Influential Citations
4
Citations
Journal
Journal of Labelled Compounds and Radiopharmaceuticals
Abstract
3-Phenoxybenzyl [1R,cis]-3–2(2,2-dichlorovinyl)-2,2-dimethyl-cyclopropanecarboxylate (I) and its [1R,trans]-isomer (II) were labelled with carbon-14 at C-2 position of the dichlorovinyl side chain for metabolic studies. The stereospecific syntheses were achieved according to the reaction scheme shown in Fig. 1. Wittig reaction of methyl [1R,cis]-3-formyl-2,2-dimethylcyclo-propanecarboxylate with carbon-14C tetrachloride followed by hydrolysis gave [1R,cis]-3-(2,2-dichlorovinyl-2–14C)-2,2-dimethylcyclopropanecarboxylic acid (VIa). Chlorination of the acid (VIa) and subsequent treatment of the resulting acid chloride with 3-phenoxybenzyl alcohol afforded 3-phenoxybenzyl [1R,cis]-3–(2,2-dichlorovinyl–2-14C)-2,2-dimethylcyclopropane-carboxylate (I) in the overall yield of 33%. Its [1R,trans]-isomer (II) was also prepared in 35% yield by the similar procedures. The specific activities of I and II were 4.30 and 3.80 mCi/mmole respectively.