To obtain the subject compounds in high yield, high purity and low in cost useful as intermediates of medicines and agrochemicals by reacting quinic acid derivatives with reagents having dehydrating capability.
The (-)-shikimic acid precursor expressed by formula II is obtained by charging the quinic acid derivatives expressed in formula I (R1, R2 are each H, an alkyl, an aryl; R3 is an acyl, an alkylsulfonyl, an arylsulfonyl; R4 is an alkyl, an alkenyl, an aralkyl), bases and solvents into a reactor and adding the reagents having dehydrating capability (for example; sulfuryl chloride, thionyl chloride, phosphorus oxychloride, iodine, etc.), to the reactor after heating to the reaction temperature of -30-25°C. Acids and solvents are added to deblock the resultant compounds at 5-50°C, purifying to obtain the compound of formula III (R3' is an acyl, an alkylsulfonyl, an arylsulfonyl), then (-)- shikimic acid is obtained by deblocking it in the presence of an acid and a base. The reaction is carried out in an inert gas atmosphere such as nitrogen.
TSURU KAZUTAKA
NAGAI SUNAO
| JPS58206564A | 1983-12-01 |