Preparation and application of (+)-(3,3-dimethyl-2-methylenenorbornan-1-yl)methyl methanesulfonate: a new and versatile chiral fenchone analogue

The preparation of (+)-(3,3-dimethyl-2-methylenenorbornan-1-yl)methyl methanesulfonate () was carried out in 2 steps, dihydroxylation and mesylation, from (−)-2-methylenebornane. Hydrolysis and reduction of gave a fenchyl alcohol () and a methylenefenchone (), respectively. Oxidation of afforded a new analogue () of the class of oxatricyclo compounds. Treatment of with NBS resulted in a Wagner–Meerwein rearrangement to produce brominated methylenebornane derivatives ( and ), which are also new compounds.