Synthesis and configurational assignment of optically active 1-hydroxyindolizidines

✍ Scribed by Constance M. Harris; Thomas M. Harris

• Publisher: Elsevier Science
• Year: 1987
• Tongue: French
• Weight: 297 KB
• Volume: 28
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)96147-1

✦ Synopsis

The four diastereomers of 1-hydroxyindolizidine have been prepared in high optical purity (>98%) by N&l$ reduction of the (+) and (-) 3-bromocamphor-8-sulfonic acid salts of l-oxoindolizidine followed by separation of the resulting diastereomeric alcohols by ion-exchange chromatography.

Irtdolizidine alkaloids are relatively rare and have for the most part received little attention; one notable exception being swainsonine (l), the active constituent of locoweecL1 The biological properties of swainsonine are currently the subject of intense study in many laboratories; the alkaloid is an inhibitor of mannosidases involved in the formation and catabolism of glycoproteins2 and is also an immunomodulator with possible applications in cancer chemotherapy.3