CATALYTIC ASYMMETRIC AMINOHYDROXYLATION PROVIDES A SHORT TAXOL SIDE-CHAIN SYNTHESIS

The p-toluenesulfonamide derivative of the C-13 side-chain of taxol wa s prepared on a one third mole scale in a single step from methyl cinn amate. The process employed is catalytic asymmetric aminohydroxylation (catalytic AA). In the present case, there is no work-up other than f iltration of the pure product which is insoluble in the reaction mixtu re. The sulfonamide protecting group is removed by acidic hydrolysis.