SYNTHESIS OF POTENTIAL METABOLITES OF ETHYL (E)-4-[2-(3,4-DIHYDRO-4,4-DIMETHYL-2H-1-BENZOPYRAN-6-YL)-1-PROPENYL]BENZOATE

Potential metabolites of ethyl (E)-4-[2-(3.4-dihydro-4,4-dimethyl-2H-1-benzopyran-6-yl)-1-propenyl]benzoate were synthesized. The new compounds include ethyl 3-[3,4-dihydro-4,4-dimethyl-2H-1-benzopyran-6-yl]crotonate, 3-[3,4-dihydro-4,4-dimethyl-2H-1-benzopyran-6-yl]crotonic acid, 3,4-dihydro-4,4-dimethyl-2H-1-benzopyran-6-carboxylic acid, 4-[3,4-dihydro-4,4-dimethyl-2H-1-benzopyran-6-yl]DELTA2-butenolide, ethyl (E)-4-[3,4-dihydro-4,4-dimethyl-2H-1-benzopyran-6-yl)-3-hydroxy-1-propenyl]benzoate, ethyl (E)-4-[2-(3,4-dihydro-4,4-dimethyl-2H-1-benzopyran-6-yl)-2-propenal]benzoate, and ethyl (E)-4-12-(3,4-dihydro-4,4-dimethyl-2H-1-benzopyran-6-yl)-2-propenoic acid]benzoate. Stereospecific oxidizing reagents and/or conditions were developed for these sensitive systems and include the use of SeO2, Clorox bleach, activated MnO2, and NaClO2 in the presence of resorcinol as a chlorine scavenger.