Abstract
The preparation of (+)-(3,3-dimethyl-2-methylenenorbornan-1-yl)methyl methanesulfonate ( 9 ) was carried out in 2 steps, dihydroxylation and mesylation, from (−)-2-methylenebornane. Hydrolysis and reduction of 9 gave a fenchyl alcohol ( 2 ) and a methylenefenchone ( 21 ), respectively. Oxidation of 9 afforded a new analogue ( 23 ) of the class of oxatricyclo compounds. Treatment of 9 with NBS resulted in a Wagner–Meerwein rearrangement to produce brominated methylenebornane derivatives ( 25 and 26 ), which are also new compounds.
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