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Citation: LIU Chang-Hui, WEN Rui-Ming, LEI Xue-Song, ZHANG Zhe. A New Synthetic Approach to Theaspirone[J]. Chinese Journal of Applied Chemistry, ;2010, 27(10): 1238-1240. doi: 10.3724/SP.J.1095.2010.90863 shu

A New Synthetic Approach to Theaspirone

Department of Chemistry and Environmental Engineering, Hunan City University, Yiyang 413000

Received Date: 22 December 2009
Revised Date: 26 March 2010

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.
- theaspirone,
- ultrasonic irradiation,
- α-ionone,
- selective reduction,
- allylic oxidation
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