Esters of 1-O-Demethylthiocolchicines: Formation of Isomers in Chloroform Solution

✍ Scribed by Peter Kerekes; Arnold Brossi; Judith L. Flippen-Anderson; Colin F. Chignell

• Book ID: 102856817
• Publisher: John Wiley and Sons
• Year: 1985
• Tongue: German
• Weight: 581 KB
• Volume: 68
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.19850680306

✦ Synopsis

Abstract

1‐O‐Acetyl‐1‐O‐demethylcolchicine, and acylated 1‐O,2‐O‐didemethylthiocolchicines, in contrast to 2‐O‐acetyl‐, 2‐O,3‐O‐diacetyl‐ and 3‐O‐acetyl analogs, showed after standing in CHCl~3~ solution significant changes in optical rotation, a duplication of ^1^H‐NMR signals, and the formation of new isomers on TLC. Solid‐state X‐ray diffraction of O‐acetylated colchinoids and thio analogs, showed out of planar arrangements of the aromatic substituents, but the analysis could not help to explain the structures of the newly formed isomers in CHCl~3~ solution.