Condensed cyclic and bridged-ring systems : part 12: a novel synthetic route to 4-p-methoxyphenyl-bicyclo[ 2.2.2 ]octan-2-ones and some bicyclo [ 3.2.1 ] octane derivatives by acid-catalyzed intramolecula

The efficacy of a new acid-catalyzed intramolecular C-alkylation has been demonstrated by the synthesis of 1-methyl-4-P -methoxyphenylbicyclo [2.2.2] octan-2-one (5) and 4-P-methoxyphenylbicyclo [2.2.2] octan-2-one (6) from easily accessible starting materials. The carbinol 30 , derived from 5, undergoes facile rearrangement leading to 1-P-methoxyphenyl-4-methyl bicyclo [3.2.1] oct-3-ene (22), which has been transformed to endo-1-P-methoxyphenyl-4-methylbicyclo [3.2.1] octan-3-one (25)