Ashok, K and Rao, GS Krishna (1993) Synthesis of 4-(4-methoxy-2,3,6-trimethylphenyl)-3-buten-2-one, a key synthon for etretinate and its metabolites. In: Indian Journal of Chemistry - Section B: Organic and Medicinal Chemistry, 32B (10). pp. 1013-1017.Full text not available from this repository. (Request a copy)
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.
|Item Type:||Journal Article|
|Additional Information:||Copyright of this article belongs to Council of Scientific & Industrial Research.|
|Department/Centre:||Division of Chemical Sciences > Organic Chemistry|
|Date Deposited:||01 Jul 2008|
|Last Modified:||27 Aug 2008 13:30|
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