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Synthesis of 4-(4-methoxy-2,3,6-trimethylphenyl)-3-buten-2-one, a key synthon for etretinate and its metabolites

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.

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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.

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
URI: http://eprints.iisc.ernet.in/id/eprint/14626

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