Organocatalytic site-selective acylation of 10-deacetylbaccatin III
Organocatalytic site-selective diversification of 10-deacetylbaccatin III, a key natural product for the semisynthesis of taxol, has been achieved. Various acyl groups were selectively introduced into the C(10)-OH of 10-deacetylbaccatin III. The C(10)-OH selective acylation was also applied to acylative site-selective dimerization of 10-deacetylbaccatin III to provide the structurally defined dimer.
CHEMICAL STUDIES OF 10-DEACETYL BACCATIN III. HEMISYNTHESIS OF TAXOL DERIVATIVES.
The chemical reactivities of 10-deacetyl baccatin III and of baccatin III, two natural products extracted from Taxus baccata L., were studied with aim of synthesizing taxol analogues having a modified side-chain at C-13, thereby restoring good binding to tubulin.
Gueritte-Voegelein, F.,Senilh, V.,David, B.,Guenard, B.,Potier, P.
p. 4451 - 4460
(2007/10/02)
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