Structure-activity relationships study at the 3'-N position of paclitaxel-part 1: Synthesis and biological evaluation of the 3'-(t)-butylaminocarbonyloxy bearing paclitaxel analogs

Article abstract of DOI:10.1016/S0960-894X(97)10142-1

An efficient syntheses of the 3'-N isomeric paclitaxel analogs, 4 and 5, are described. A highly diastereoselective Sharpless asymmetric dihydroxylation reaction is utilized to establish the required (2'R,3'S) stereochemistry on the C-13 side chain. Both of the 3'-N modified analogs 4 and 5 were found to be cytotoxic in vitro, Analog 4 also displayed comparable in vivo activity to that of paclitaxel in the ip M-109 tumor model.