𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Rearrangement of vindoline and derivatives in superacidic media

✍ Scribed by Cécile Lafitte; Marie-Paule Jouannetaud; Jean-Claude Jacquesy; Alain Duflos

Book ID
104209118
Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
586 KB
Volume
55
Category
Article
ISSN
0040-4020

No coin nor oath required. For personal study only.

✦ Synopsis

SbF5 at O°C, vindoline la and its deaeetyl derivative l.~b yield the cathovaline like compounds 4 and 5_., respoctively, and the furanic diastereoisemers _2 and 3. Flunm derivatives (20S)-10b-d rearrange in supemcids to 4 (92%), _5 (60%) and to lac~ne 11 (58%), respectively, whereas the (20R) analogs are completely unresctive. This last result can be accounted for by intervening of a reactive conformation of the fluoroethyl group in the (20S) series, the concsponding one in the (20R) series being disfavored for steric reasons.

📜 SIMILAR VOLUMES

ChemInform Abstract: Rearrangement of Vi
ChemInform Abstract: Rearrangement of Vindoline and Derivatives in Superacidic Media.
✍ Cecile Lafitte; Marie-Paule Jouannetaud; Jean-Claude Jacquesy; Alain Duflos 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 32 KB 👁 2 views

Rearrangement of Vindoline and Derivatives in Superacidic Media. -Whereas the (20S)-fluoro derivatives (VI)-(VIII) rearrange to different products [(III), (V), or (IX)], the (20R) analogues are completely unreactive.