ChemInform Abstract: Enantioselective Synthesis of (-)-Pumiliotoxin C from a Chiral Amino Ester and an Acetylenic Sulfone that Acts as an Alkene Dipole Equivalent.

✍ Scribed by T. G. BACK; K. NAKAJIMA

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 31 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199906196

✦ Synopsis

Enantioselective Synthesis of (-)-Pumiliotoxin C from a Chiral Amino Ester and an Acetylenic Sulfone that Acts as an Alkene Dipole Equivalent.

-A new synthesis of the natural enantiomer of the dendrobatid alkaloid pumiliotoxin C (VII) which acts as reversible blocker of the nicotinic acetylcholine receptor channel is presented. Key feature is the utilization of sulfone (II) as an alkene dipole equivalent. A new preparation of the known intermediate (I) is also developed, based on a kinetic resolution using PLE and a Curtius rearrangement [yield of compound (V) given in mg]. -(BACK, T.