PURPOSE: To obtain trans-3,4-disubstituted γ-lactone compounds having a high optical purity in simple steps by using levoglucosenone as a starting substance and forming a lactone ring using the Baeyer-Villiger oxidative reaction.
CONSTITUTION: An alkyl group R1 (R1 is alkyl or alkenyl) is added to an enone part of levoglucosenone expressed by formula I that is a thermal decomposition product of cellulose to provide a compound expressed by formula II, which is then subjected to the Baeyer-Villiger oxidation using a peracid (e.g. peracetic acid). Thereby, a lactone ring is formed to afford a compound expressed by formula III. The OH of the resultant compound expressed by formula III is subsequently converted into a leaving group OR2 to provide a compound expressed by formula IV. Alkylation or alkenylation is then carried out in the presence of a copper salt (e.g. copper iodide) to afford a compound expressed by formula V, which is an aromatic ingredient in whiskies, etc., and utilized as a pheromone in the insect kingdom.
MATSUSHITA HAJIME
KAWAKAMI HIROSHI
KOSEKI YUKIFUMI
