No abstract

Dialkylaluminium aryloxide in combination with a tertiary amine was found to be a good reagent for regioselective aldol condensation of methyl ketones at the methyl side. Regioselective aldol condensation of 2-octanone was carried out using diisobutylaluminium phenoxide–pyridine. The intramolecular aldol condensation of 2,15-hexadecanedione promoted by the same reagent gave a mixture of dehydromuscones in 65% yield. Its hydrogenation produced muscone.

No abstract

8-Acetoxy-1,6-octadiene was oxidized with PdCl2/CuCl/O2 to give 8-acetoxy-6-octen-2-one. Hydrolysis and hydrogenation of the ketone produced 8-hydroxy-2-octanone, which was converted to the tosylate after protection of the ketone. The tosylate was converted into the iodide and bromide. The bromide was converted into the Grignard reagent, and coupled with the iodide by the catalysis of CuI coordinated by 2,2′-bipyridyl to give 2,15-hexadecanedione.

The terminal double bond of 3,8-nonadienoate was oxidized to methyl ketone with a catalyst system of PdCl2/CuCl/O2 and the internal double bond was reduced to give 8-oxononanoate, which was hydrolyzed to 8-oxononanoic acid. The Kolbe electrolysis of the acid produced 2,15-hexadecanedione in a high yield.