Synthesis of novel taxoid analogue containing sulfur group on C-13 side-chain: 2′-deoxy-2′-epi-mercaptopaclitaxel

Abstract

Paclitaxel analogues with a thiol group in place of the hydroxyl group on the C-13 side-chain constitute an interesting avenue of research for the study of new taxoid compounds. A synthetic route for the preparation of 2′-deoxy-2′-epi-mercaptopaclitaxel with high ee has been developed. The key step is the regio-controlled ring-opening reaction of the trans-oxazoline derivative with thiolacetic acid, which allows the introduction of the sulfur-containing group onto the side-chain. © 2003 Elsevier Ltd. All rights reserved.