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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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 |
|---|---|
| Publication: | Indian Journal of Chemistry - Section B: Organic and Medicinal Chemistry |
| Publisher: | Council of Scientific & Industrial Research |
| 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.ac.in/id/eprint/14626 |
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