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Synthesis based on cyclohexadienes: Part 30 - Syntheses of 2-nor-cedrene and some analogues of funebrene

Hariprakasha, HK and Sathya Shanker, P and Rao, Subba SR (2000) Synthesis based on cyclohexadienes: Part 30 - Syntheses of 2-nor-cedrene and some analogues of funebrene. In: Indian Journal of Chemistry - Section B: Organic and Medicinal Chemistry, 39 (2). pp. 94-102.

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Official URL: http://onlinelibrary.wiley.com/doi/10.1002/chin.20...

Abstract

A novel method for the construction of tricyclo[5.3.1.0(1,5)]undecane and tricyclo[6.3.1.0(1,6)]dodecane frame work has been developed. Thus the alcohols 6, 18, 21 and 29 undergo Lewis acid-catalysed rearrangement to the tricyclic ketones 5, 19, 22 and 30. Dehydrogenation of 22 to the enone 23 proves the synchronous anti-migration of the methanobridge during the skeletal rearrangement. Finally, one carbon homologation of the ketones 5 and 19 leads to the syntheses of 2-norcedrene 4 and some analogues of funebrene 20 and 30.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to National Institute of Science Communication and Information Resources.
Keywords: Terpenes;rearrangement.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 25 Aug 2010 05:52
Last Modified: 25 Aug 2010 05:52
URI: http://eprints.iisc.ernet.in/id/eprint/31273

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