Abstract
Abstract Our earlier studies established that: 1) 2-octyl- and 2-phenyl-4H-1,3,2-benzodioxaphosphorin 2-oxides (octyl- and phenyl-BDPOs) induce delayed neuropathy in adult hens at 3 and 200 mg/kg, respectively; 2) phenyl-BDPO also significantly potentiates the acute toxicity of the insecticide malathion to mice; 3) the (Rp) and (Sp) enantiomers of these compounds, resolved on a mg scale by chiral HPLC, differ in potency by 92- and 137-fold, respectively, as inhibitors of neuropathy target esterase. In order to further study the stereospecificity in their toxic effects, the individual enantiomers of octyl- and phenyl-BDPOs are prepared here by a general method of asymmetric synthesis from the corresponding TLC-resolved diastereomeric precursors (Rp)- and (Sp)-methyl N-[2-hydroxymethylphenoxy(octyl or phenyl)phosphonyl] L-prolinates through acid-catalyzed intramolecular cyclization. This occurs under mild conditions in high yields and involves inversion of configuration at phosphorus. HPLC with the CHIRALCE...
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