Studies on Streptomyces Antibiotic, Cycloheximide. VIII. Hydroxycarbonylation of Optically Active 2, 4-Dimethylcyclohexanone and Chemical Correlation of the Products. (1)

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The condensation of cis-d-2, 4-dimethylcyclohexanone with para-substituted benzal-dehyde was carried out using tetramethylammonium hydroxide (aldol condensation) or N-methylanilinomagnesium bromide (Nielsen's condensation) as a basic condensation agent. Aldol and Nielsen's condensation gave the stereoisomeric hydroxycarbonylation products, ketol-As and ketol-Ns, respectively, the former showing positive [α]_D values and the latter, negative values.