Synthesis of potential metabolites of ethyl (E)-4-[2-(3,4-dihydro-4,4- dimethyl-2H-1-benzopyran-6-yl)-1-propenyl]benzoate

Article abstract of DOI:10.1002/jps.2600820522

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]Δ²-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-[2-(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.