| 摘要 |
PURPOSE:To obtain the subject compound, excellent in optical purity and useful as physiologically active compounds, etc., in good yield according to simple operation by asymmetrically epoxidizing dimethyldioxy(hydroxypropenyl)one, reducing the epoxidized compound and subjecting the reduction product to oxidative cleavage of an olefin with ozone gas. CONSTITUTION:2,2-Dimethyl-1,3-dioxy-6-(3-hydroxy-1-propenyl)-4-one expressed by formula I is asymmetrically epoxidized in the presence of a tetra- alkoxytitanium and a diester of tartaric acid using an oxidizing agent such as tert-butyl hydroperoxide to synthesize an optically active compound expressed by formula II (* indicates asymmetric carbon), which is then catalytically reduced in the presence of a catalyst such as palladium carbon in an atmosphere of hydrogen to provide a compound expressed by formula III. The obtained compound expressed by formula III is then subjected to oxidative cleavage of an olefin with ozone gas to afford the objective compound expressed by formula IV. |
