A CHEMOSELECTIVE APPROACH TO FUNCTIONALIZE THE C-10 POSITION OF 10-DEACETYLBACCATIN .3. SYNTHESIS AND BIOLOGICAL PROPERTIES OF NOVEL C-10 TAXOL(R) ANALOGS
J. Kant et al., A CHEMOSELECTIVE APPROACH TO FUNCTIONALIZE THE C-10 POSITION OF 10-DEACETYLBACCATIN .3. SYNTHESIS AND BIOLOGICAL PROPERTIES OF NOVEL C-10 TAXOL(R) ANALOGS, Tetrahedron letters, 35(31), 1994, pp. 5543-5546
A chemoselective approach to functionalize the C-10 position of 10-dea
cetyl baccatin III, a key intermediate for the semi-synthesis of pacli
taxel, is described. The chemistry provides an easy access to a variet
y of C-10 hydroxyl derivatives, such as, ethers, esters, carbonates, c
arbamates, and sulfonates under mild conditions. The C-10 modified bac
catin derivatives were further employed in the synthesis of never biol
ogically active Taxol(R) analogues.