1980 Volume 44 Issue 3 Pages 625-629
Novel syntheses of isolaurene (1), an isomer of laurene (2) found in algae, and its related compounds were performed from cyclotene (3). Benzylated cyclotene (4) was allowed to react with p-tolyl-magnesium bromide to give 5-methyl-2-p-tolyl-2-cyclopentenone (6). Hydrogenation of 6 over palladium charcoal, followed by methylation with one equivalent of methyl iodide gave 2, 5-dimethyl-2 p-tolyl-cyclopentanone (8), whereas treatment with 3 equivalents of methyl iodide gave 2-p-tolyl-2, 5, 5-trimethylcyclopentane (10). Both 8 and 10 were treated with a large excess of methyl lithium to afford the corresponding alcohols (9) and (11), dehydration of which, in an acidic medium, gave 1 and 1-methylene-2-p-tolyl-2, 5, 5-trimethylcyclopentane (12), respectively. Compound 10 is a structural isomer of cuparenone (15) found in the wood of an Indian plant.
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