Methylcyclonon-5-en-l-one (5) was obtained by treatment of an 85:15 mixture of 4a-(4a) and 4/3-(tosyloxy)-7a/8-hydroxy-3ad-methyl-3a,4,5,6,7,7a-hexahydroindan (4e) with potassium ferf-butoxide in ferf-butyl alcohol. The corresponding E isomer (6) was also produced in a small quantity in this experiment and in reasonable yield when 4/3-(mesyloxy)-7al8-hydroxy-3alS-methyl-3a,4,5,6,7,7a-hexahydroindan (4b) was reacted under similar conditions. However, the E enone was not isolated in pure form. The hexahydroindandiols which were used to prepare the monosulfonates were obtained by reduction of 3a,7a-epoxy-3a,4,5,6,7,7a-hexahydro-4-indanone (7) with lithium and liquid ammonia followed by addition of methyl iodide to give 7a/3-hydroxy-3a/3-methyl-3a,4,5,6,7,7a-hexahydro-4-indanone (8) and then reduction of the carbonyl group in 8 with metal hydrides or lithium in liquid ammonia.
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