Synthesis of (±)-Strychnofoline via a Highly Convergent Selective Annulation Reaction

✍ Scribed by Andreas Lerchner; Erick M. Carreira

• Publisher: John Wiley and Sons
• Year: 2006
• Tongue: English
• Weight: 502 KB
• Volume: 12
• Category: Article
• ISSN: 0947-6539
• DOI: 10.1002/chem.200600957

✦ Synopsis

Abstract

Studies aimed at preparing (±)‐strychnofoline by total synthesis are detailed. The route described makes use of a recently developed MgI~2~‐mediated ring‐expansion reaction of spiro[cyclopropan‐1,3′‐oxindole] with a cyclic disubstituted aldimine. The ring‐expansion product was formed as a single diastereoisomer in 55 % yield, possessing the same stereochemical pattern found in strychnofoline. In addition, our synthetic effort has led to the development of new reaction methodology to access 3,4‐disubstituted cyclic aldimines.