Catalytic asymmetric aminohydroxylation provides a short taxol side-chain synthesis.

G Li, K B Sharpless

Index: Acta Chem. Scand. 50 , 649, (1996)

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Abstract

The p-toluenesulfonamide derivate of the C-13 side-chain of taxol was prepared on a one third mole scale in a single step from methyl cinnamate. The process employed is catalytic asymmetric aminohydroxylation (catalytic AA). In the present case, there is no work-up other than filtration of the pure product which is insoluble in the reaction mixture. The sulfonamide protecting group is removed by acidic hydrolysis.