Taxol and taxotere: discovery, chemistry, and structure-activity relationships

The final acylation step in Taxol biosynthesis: Cloning of the taxoid C13-side-chain N -benzoyltransferase from Taxus

“…Taxol is presently manufactured semisynthetically by coupling the advanced naturally occurring taxoid 10-deacetylbaccatin III, isolated from the needles of Taxus baccata, to a synthetic side-chain precursor (2,3). The reliance on the isolation of natural products from Taxus species, or Taxusderived cell cultures, will continue for the foreseeable future because total synthesis of the drug is not commercially viable.…”

Molecular cloning and heterologous expression of the C-13 phenylpropanoid side chain-CoA acyltransferase that functions in Taxol biosynthesis

“…2), a naturally occurring biosynthetic precursor of Taxol, as the principal means of producing the drug to meet increasing demand (8)(9)(10). This semisynthetic method, however, involves several steps, including silyl protection and acetylation of 10-deacetylbaccatin III to afford 7-O-protected baccatin III, synthetic attachment of the N-Bz phenylisoserine side chain at the C-13 hydroxyl, and, finally, deprotection to yield Taxol (see Fig.…”

A late phase II study of RP56976 (docetaxel) in patients with advanced or recurrent breast cancer

“…The new anti-neoplastic taxoid, RP56976 (docetaxel, Ndebenzoyl-N-tert-bytoxycarbonyl-10-deacetyl taxol), has been semisynthesised from the precursor (10-deacetylbaccatin III) derived from the needles of the European yew, Taxus baccata, by Rhone-Poulenc Rorer and Centre National de la Recherche Scientifique, France (Ringel and Horwitz, 1991;Guenard et al, 1993). This agent is an analogue of Taxol (paclitaxel), but has a more hydrophilic chemical structure and requires cremophor as a solvent.…”