A short synthesis of troglitazone: an antidiabetic drug for treating insulin resistance.
Troglitazone was obtained in 5 steps from 4-bromo-1,1-dimethoxy-3-methylbut-2-ene with an overall yield of 7.5%. The formation of the chromane ring was achieved by condensing an unsaturated acetal with trimethylhydroquinone in the presence of bis(trifluoromethylsulfonyl)imide.
Cossy
J
J
Laboratoire de Chimie Organique, associé au CNRS, ESPCI, Paris, France. janine.cossy.espci.fr.
Menciu
C
C
Rakotoarisoa
H
H
Kahn
P H
PH
Desmurs
J R
JR
D002839:Chromans / Q000138:chemical synthesis*; D007004:Hypoglycemic Agents / Q000138:chemical synthesis*; D007333:Insulin Resistance; D013844:Thiazoles / Q000138:chemical synthesis*; D045162:Thiazolidinediones; D000077288:Troglitazone
D002839:Chromans; D007004:Hypoglycemic Agents; D013844:Thiazoles; D045162:Thiazolidinediones; D000077288:Troglitazone