PURPOSE: To readily produce a 3,4-disubstituted-cis-γ-lactone showing much excellent aroma than trans-isomer, useful as spices, especially as a fragrant composition of whiskey and wine, selectively, in high yield and readily.
CONSTITUTION: A substituent group R2 (R2 is straight-chain or branched alkyl, alkenyl or alkynyl) is introduced to the 2-position of a compound of formula I to give a compound of formula II. An ordinary OH-protecting group R3 is introduced to OH at the 1-position of the compound of formula II to give a compound of formula III. Then the olefin part of the compound of formula III is oxidatively cleft to give a compound of formula IV. This compound is deprotected and a lactone is formed to give a compound of formula V. Then COOH of the compound is selectively reduced to give a compound of formula VI and an ordinary eliminable group R4 is introduced to OH of the compound of formula VI to give a compound of formula VII. Further its eliminable group R4 is replaced with a substituent group R1 to selectively give a 3,4-disubstituted- cis-γ-lactone of formula VIII (R1 is each group in R2).
KAWAKAMI HIROSHI
MATSUSHITA HAJIME
