Electrochemical reduction of taxoids: Selective preparation of 9-dihydro-, 10-deoxy- and 10-deacetoxy-taxoids

✍ Scribed by Jean-Pierre Pulicani; Jean-Dominique Bourzat; Hervé Bouchard; Alain Commerçon

• Publisher: Elsevier Science
• Year: 1994
• Tongue: French
• Weight: 465 KB
• Volume: 35
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)73303-x

✦ Synopsis

AWtract: The electmchomical reduction of do&axe1 in methanol in the presence of ammoniom chloride leads to 9amI 3 and whydro-docetaxe I 4. under the same conditions, the electmchemical reduction ofpaclitaxel gives 10deacetoxy-Paclitaxe17. Calcium chloride as well as magnesium and ceriwn chloride, and to some extent strontium and lithium chloride, favor 1Odehydroxyhuion in the docetaxel series. AU those docemxel analogs retain biological activity.

Semisynthetic taxoid docetaxel (Taxotere@, 1) and natural product pa&axe1 (Taxol@, 2) are structurally unique diterpenoids exhibiting high antitumor activity'. Results from ongoing clinical trials for