Method of producing cis-whiskey lactone

摘要

PCT No. PCT/JP91/01780 Sec. 371 Date Aug. 27, 1992 Sec. 102(e) Date Aug. 27, 1992 PCT Filed Dec. 27, 1991 PCT Pub. No. WO92/12143 PCT Pub. Date Jul. 23, 1992.After the lactone portion of trans-whiskey lactone is hydrolyzed with potassium hydroxide, this portion is reacted with isopropyl bromide and mixed with an alkyl group, thereby obtaining isopropyl (3S,4S)-4-hydroxy-3-methyloctanoate. Then, the isopropyl (3S,4S)-4-hydroxy-3-methyloctanoate is reacted with diethyl azodicarboxylate in the presence of triphenylphosphine and azodicarboxylate, thereby obtaining isopropyl (3S,4S)-4-(3',5'-dinitrobenzoyloxy)-3-methyloctanoate. The isopropyl (3S,4S)-4-(3',5'-dinitrobenzoyloxy)-3-methyloctanoate is hydrolyzed in 2% potassium hydroxide, and as a result, cis-whiskey lactone (A) represented by the following general formula is obtained. According to this method, cis-whiskey lactone, one of the perfume components of whiskey and wine, can be produced selectively and easily. <IMAGE> (A)