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

✍ Scribed by Xin Qi; Sang-Hyeup Lee; Juyoung Yoon; Yoon-Sik Lee

• Publisher: Elsevier Science
• Year: 2003
• Tongue: French
• Weight: 124 KB
• Volume: 59
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(03)01098-6

✦ Synopsis

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 0 -deoxy-2 0 -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.