The title taxane derivative is prepared by two related ways. Taxane (I) is condensed with azetidinone (II) in the presence of lithium hexamethyldisilazide to afford ester (III). The triisopropylsilyl protecting group of (III) is then removed by using a solution of tetrabutylammonium fluoride in THF, yielding (IV). Dihydroxylation of the vinyl group of (IV) with N-methylmorpholine N-oxide in the presence of osmium tetroxide produces diol (V), which is subsequently cleaved to aldehyde (VI) by means of NaIO4. Finally, reductive amination of aldehyde (VI) with dimethylamine and NaBH3CN gives rise to the target amine.
Similarly, condensation of taxane (I) with azetidinone (II) in the presence of lithium hexamethyldisilazide affords ester (III). The terminal vinyl group of (III) is converted to aldehyde (IV) by dihydroxylation with NMMO/OsO4, followed by oxidative cleavage with NaIO4. Reductive amination of aldehyde (IV) with dimethylamine and NaBH3CN yields amine (V). Selective catalytic hydrogenation of the disubstituted olefin of (V) produces taxane (VI), which is finally O-desilylated employing tetrabutylammonium fluoride in cold THF.