Total Synthesis of (−)-Crinine. Use of Tandem Cationic Aza-Cope Rearrangement/Mannich Cyclizations for the Synthesis of Enantiomerically Pure Amaryllidaceae Alkaloids

✍ Scribed by Larry E. Overman; Soji Sugai

• Publisher: John Wiley and Sons
• Year: 1985
• Tongue: German
• Weight: 350 KB
• Volume: 68
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.19850680324

✦ Synopsis

Abstract

The total synthesis of enantiomerically pure (−)‐crinine (1) in 10 steps and 6% overall yield from cyclopentene oxide is reported. The key step was the rearrangement of 7 upon reaction with AgNO~3~ at 25°C to give cis‐perhydroindolone 8 in 81% yield.