Chemical studies of 10-deacetyl baccatin III

Studies on the biosynthesis of taxol: the taxane carbon skeleton is not of mevalonoid origin.

“…Taxoid is the generic name of of a large class of diterpenes like taxin (7,8) which was first isolated from the European yew tree Taxus baccata. Two members of this class of compounds, taxol (9) and its semisynthetic analog, Taxotere (10), are used successfully for chemotherapy of solid tumors, especially in cases of resistence against classical cytostatic agents.…”

Antineoplastic drugs and their analysis: a state of the art review

“…A solution was introduced in the '80s by Pierre Potier (also author of the discovery of vinorelbine) with the hemisynthesis of paclitaxel from a precursor (non-cytotoxic) available from a renewable source (Taxus baccata needles). 425 This route also gave rise to another taxane with anticancer properties, docetaxel. Slightly soluble in water, docetaxel injectable formulations contain ethanol and polysorbate 80 (a less toxic excipient).…”

Organocatalytic Site-Selective Acylation of 10-Deacetylbaccatin III

“…The relative reactivity of the four hydroxy groups of 1 toward acetic anhydride in pyridine has been studied by Guéritte-Voegelein and co-workers, and suggested to be in the order of C(7)-OH>C(10)-OH>C(13)-OH>C(1)-OH. 12) Greene reported C(7)-OH-selective silylation by making use of the subtle difference in the reactivities of the hydroxy groups, which enabled a highly efficient semisynthesis of 4. 13) Holton found that acylation took place at the C(10)-OH selectively using excess amount of acetic anhydride and Lewis acids (ZnCl 2 , CeCl 3 ) in the absence of pyridine to achieve selective synthesis of baccatin III (2).…”