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Aza-Cope Rearrangement—Mannich Cyclizations for the Formation of Complex Tricyclic Amines: Stereocontrolled Total Synthesis of (.+-.)-Gelsemine.

✍ Scribed by William G. Earley; Jon E. Jacobsen; Andrew Madin; G. Patrick Meier; Christopher O'Donnell; Taeboem Oh; David W. Old; Larry E. Overman; Matthew J. Sharp

Publisher: John Wiley and Sons
Year: 2006
Weight: 10 KB
Volume: 37
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.200622195

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

✍ Larry E. Overman; Soji Sugai 📂 Article 📅 1985 🏛 John Wiley and Sons 🌐 German ⚖ 350 KB 👁 1 views

## 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.