Synthese von (1α,7α,8β)-(±)-7-Hydroxy-1-(hydroxymethyl)pyrrolizidin, der Necin-Baserac-Platynecin

✍ Scribed by Röder, Erhard ;Bourauel, Thomas ;Wiedenfeld, Helmut

• Book ID: 102366124
• Publisher: John Wiley and Sons
• Year: 1990
• Tongue: English
• Weight: 264 KB
• Volume: 1990
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.1990199001113

✦ Synopsis

Synthesis of (1α,7α,8β)‐(±)‐7‐Hydroxy‐1‐(hydroxymethyl)pyrrolizidin, the Necine rac‐Platynecine

rac‐Platynecine (rac‐7) can easily be obtained in high yields from diethyl (±)‐cis‐2,3‐pyrrolidinedicarboxylate (rac‐1) by N‐alkylation to ethyl (±)‐cis‐2,3‐bis(ethoxycarbonyl)‐1‐pyrrolidinepropionate (rac‐2), Dieckmann reaction to ethyl (1α,8β)‐(±)‐6‐ethoxycarbonyl‐7‐oxo‐1‐pyrrolizidinecarboxylate (rac‐3), subsequent saponification, decarboxylation, reduction to (1α,7α,8β)‐(±)‐pyrrolizidine‐1,7‐carbolactone (rac‐6), and further reduction to the desired title compound rac‐7.