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-1H-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]delta 2-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.
Sunthankar
P S
PS
Department of Chemistry, Oklahoma State University, Stillwater 74078.
Berlin
K D
KD
Nelson
E C
EC
Thorne
R L
RL
Geno
P W
PW
Archer
J C
JC
Rolf
L L
LL
Bartels
K E
KE
D001578:Benzopyrans / Q000138:chemical synthesis* / Q000378:metabolism; D007202:Indicators and Reagents; D010084:Oxidation-Reduction; D012176:Retinoids / Q000138:chemical synthesis* / Q000378:metabolism; D013237:Stereoisomerism
D001578:Benzopyrans; D007202:Indicators and Reagents; D012176:Retinoids; C082813:ethyl 4-(2-(3,4-dihydro-4,4-dimethyl-2H-1 benzopyran-6-yl)-1-propenyl)benzoate