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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.

Synthesis of isolaurene and its related compounds from cyclotene.