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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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 |
|---|---|
| Publication: | Indian Journal of Chemistry - Section B: Organic and Medicinal Chemistry |
| Publisher: | National Institute of Science Communication and Information Resources |
| 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.ac.in/id/eprint/31273 |
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