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.Full text not available from this repository.
A novel method for the construction of tricyclo[188.8.131.52(1,5)]undecane and tricyclo[184.108.40.206(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.|
|Department/Centre:||Division of Chemical Sciences > Organic Chemistry|
|Date Deposited:||25 Aug 2010 05:52|
|Last Modified:||25 Aug 2010 05:52|
Actions (login required)