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.
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