PURPOSE: To easily and selectively synthesize a natural-type ciswhiskey lactone having high utility by inverting the steric configuration of the 4-butyl group of 4-trans-whiskey lactone via three steps.
CONSTITUTION: The lactone part of 3,4-trans-whiskey lactone of formula I is hydrolyzed and an alkyl is added thereto to obtain a 3,4-trans compound of formula II (R is alkyl). The compound is made to react with an acyl compound in the presence of triphenylphosphine and an azodicarboxylic acid ester. Finally, the obtained 3,4-cis-compound of formula III (R' is acyl) is hydrolyzed and then lactonized to obtain the 3,4-cis-whiskey lactone of formula IV. (3R,4 S)-3-methyl-4-octanolide can be converted into (3R,4R)-3-methyl-4-octanolide by the process similar to the above reactions. The fragrance of a natural-type whiskey lactone existing in whiskey, wine, etc., is superior to that of other whiskey lactones.
MATSUMOTO KATSUYA (JP)
KOSEKI KOSHI (JP)
KAWAKAMI HIROSHI (JP)
MATSUSHITA HAJIME (JP)
YOSHIKOSHI HAJIME (JP)
OKANIWA MASAKAZU (JP)
YUKI GOSEI YAKUHIN KOGYO KK (JP)
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