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Terpenoids. Part LXXXI. Synthesis of $(\pm)$-pterosin-M and onitin

Raju, B and Rao, Krishna GS (1987) Terpenoids. Part LXXXI. Synthesis of $(\pm)$-pterosin-M and onitin. In: Indian Journal of Chemistry, Sect. B: Organic Chemistry including Medicinal Chemistry, 26 (10). pp. 914-916.

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Abstract

2,4-Dimethyl-3-carbomethoxymethylanisole on $LiAlH_4$ reduction gives an alcohol which is converted into its Me ether. Formylation of the latter, followed by Horner reaction yields the unsaturated ester I which is converted by hydrolysis and hydrogenation into a dihydrocinnamic acid. Cyclodehydration of the latter with HF leads to the indanone di-Me ether II which on demethylation with HBr/AcOH affords $(\pm)$-pterosin-M (III; R = H). Methylation of II, followed by ether cleavage with HBr/AcOH gives onitin (III; R = Me).

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: 18 Apr 2008
Last Modified: 27 Aug 2008 13:20
URI: http://eprints.iisc.ernet.in/id/eprint/13759

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