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Synthesis of optically active carbon 14 cyphenothrin carbon 14 labeling at the carbonyl carbon



Synthesis of optically active carbon 14 cyphenothrin carbon 14 labeling at the carbonyl carbon



Radioisotopes 35(3): 103-108



Optically active cyphenothrins, .alpha.-cyano-3-phenoxybenzyl (1R)-cis- and (1R)-trans-chrysanthemates were labelled with 14C at the carbonyl carbon for use in metabolic studies. Ethyl glycinate-1-14C hydrochloride (6), prepared from potassium cyanide-14C (2) in the three steps, was condensed with 2,5-dimethyl-2,4-hexadiene via the diazo intermediate to give ethyl cis, trans-chrysanthemate-14C (7). Hydrolysis of the ester 7 followed by geometrical separation gave cis- and trans-chrysanthemic-14C acid (8a and 8b). Each geometrical isomer (8a or 8b), was optically resolved to afford (1R)-cis- or (1R)-trans-chrysanthemic-14C acid (8c or 8d). Esterification of 8c and 8d with .alpha.-cyano-3-phenoxybenzyl bromide (9) gave (1R)-cis- and (1R)-trans-cyphenothrin-(carbonyl-14C) (1a and 1b) in the yields of 4 and 6% from 2, respectively.

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