Abstract
The enantiomerically pure (-)-(1R,3S,4S,6R,8R)-4-bromo-3-methoxy-2-oxatricyclo[4.3.1.0(3,8)]decan-10-one 1 was transformed into a chiral C2-symmetric molecule (+)-(1R,3R,5R,7R)-2-oxatricyclo[3.3.1.1(3,7)]decane-4,8-dione (2-oxaadamantane-4,8-dione) 2 by a silver nitrate promoted molecular rearrangement/debromination reaction. The Cotton effect in the circular dichroism spectrum of the C2-symmetric (+)-2-oxaadamantane-4,8-dione was studied to prove the absolute configuration.
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