Abstract:

An edible perfume theaspirone, 1-oxa-8-oxo-2,6,10,10-tetramethyl-spiro-[4,5]-6-decene, was synthesized from α-ionone with 52.6% overall yield via six steps including epoxiation by metachloroperbenzoic acid, ring-opening in the presence of sodium methoxide, selective reduction of carbon-carbon double bond catalyzed by Pd/C with ammoniumformate under ultrasonic irridiation, then reduction with sodium borohydride, intramolecular cyclodehydration and allylic oxidation catalyzed by acetylacetone cobalt(Ⅱ) with oxygen gas. The structures and compositions of the product and some intermediates were characterized by IR, 1H NMR, MS and elemental analysis.

Key words: theaspirone, ultrasonic irradiation, α-ionone, selective reduction, allylic oxidation