TY - JOUR
T1 - Chemical Synthesis and Biological Evaluation of C-2 Taxoids
AU - Nicolaou, K. C.
AU - Renaud, J.
AU - Nantermet, P. G.
AU - Couladouros, E. A.
AU - Guy, R. K.
AU - Wrasidlo, W.
PY - 1995
Y1 - 1995
N2 - An efficient, general method for the synthesis of 1,2-hydroxy esters by regioselective nucleophilic opening of 1,2-cyclic carbonate systems has been developed. A reliable and practical route giving access to the taxoid carbonate 2 from the readily available 10-deacetylbaccatin III (13) has been established. Nucleophilic opening of the carbonate 2 with a variety of nucleophiles provided a number of novel C-2 Taxols. Water-soluble taxoid onium salts (e.g., 31e, 31n, 32, and 34b) were also synthesized and studied. A selected number of taxoids were subjected to cytotoxicity and tubulin polymerization assays as well as in vivo studies. The results of these studies are reported herein.
AB - An efficient, general method for the synthesis of 1,2-hydroxy esters by regioselective nucleophilic opening of 1,2-cyclic carbonate systems has been developed. A reliable and practical route giving access to the taxoid carbonate 2 from the readily available 10-deacetylbaccatin III (13) has been established. Nucleophilic opening of the carbonate 2 with a variety of nucleophiles provided a number of novel C-2 Taxols. Water-soluble taxoid onium salts (e.g., 31e, 31n, 32, and 34b) were also synthesized and studied. A selected number of taxoids were subjected to cytotoxicity and tubulin polymerization assays as well as in vivo studies. The results of these studies are reported herein.
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U2 - 10.1021/ja00114a005
DO - 10.1021/ja00114a005
M3 - Article
AN - SCOPUS:0000585732
SN - 0002-7863
VL - 117
SP - 2409
EP - 2420
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 9
ER -