K. Ashok, G. Rao
1993
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Journal
Indian Journal of Chemistry Section B-organic Chemistry Including Medicinal Chemistry
Abstract
A synthetic route to 4-(4-methoxy-2,3,6-trimethylphenyl)-3-buten-2-one, a valuable synthon to etretinate (I), a potent antipsoriatic drug is described. The keto acids II (R = Me, H) obtained from 2,5-dimethylanisole by acylation with methylsuccinic and succinic anhydrides, respectively, are elaborated separated to the identical hoxytrimethyl dihydronaphthalene (III) which on ozonolysis furnishes the ring opened arylketoaldehyde IV (R = H, R1 = CHO). Strategic manipulation of the keto and aldehyde functions of IV (R = H, R1 = CHO) leads to the arylbutanone IV (R = H, R1 = Me). Side chain bromination of IV (R = H, R1 = Me) gives the bromoketone IV (R = Br, R1 = Me) which provides on dehydrobromination the key synthon.