Abstract
Selenium dioxide oxidises 2,7 - epoxydiisophoran - 1 - ol - 3 - one to the corresponding yellow 3,4-diketone. This is reduced to diisophor - 2(7) - en - 1 - ol - 3 - one (“diisophorone”) by Zn in acetic acid or on catalytic hydrogenation, or to 2,7 - epoxydiisophorane - 1,3,4 - triol by LAH or NaBH 4. Alkaline H 2O 2 cleaves ring A of the 3,4-diketone, providing a degradation of the diisophorane- to the bicyclo[3.3.1]nonane-system. The resulting 3 - (2' - carboxy - 2',2' - dimethyl)ethyl -2, 3 - epoxy -1 - hydroxy - 5,7,7 - trimethylbicyclo(3.3.1]nonane - 2- carboxylic acid is convertible into its dimethyl ester by the action of diazomethane.
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