Easy synthesis of 7-alkylbicyclo[3.3.1]non-6-en-3-ones by silica gelpromoted fragmentation of 3-alkyl-2-oxaadamant-1-yl mesylates

Article abstract of DOI:10.1016/0040-4020(96)00217-7

A synthesis of 7-alkylbicyclo[3.3.1]non-6-en-3-ones 4b-f and 4j,k by reaction of the corresponding 3-alkyl-2-oxaadamant-1-yl mesylates 3 with silica gel in methylene chloride at room temperature, is described. The method failed to give enones 4a,g and the