Catalytic asymmetric aminohydroxylation provides a short taxol side-chain synthesis.
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.
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Department of Chemistry, Scripps Research Institute, La Jolla, CA 92037, USA.
Sharpless
K B
KB
D002934:Cinnamates / Q000737:chemistry; D006900:Hydroxylation; D015394:Molecular Structure; D017239:Paclitaxel / Q000138:chemical synthesis* / Q000737:chemistry; D013449:Sulfonamides / Q000138:chemical synthesis; D014050:Toluene / Q000031:analogs & derivatives / Q000138:chemical synthesis; D000096926:Benzenesulfonamides
D002934:Cinnamates; D017239:Paclitaxel; D013449:Sulfonamides; D014050:Toluene; C025385:methyl cinnamate; C025417:4-toluenesulfonamide; D000096926:Benzenesulfonamides