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

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

Book ID: 115314137
Publisher: American Chemical Society
Year: 2005
Tongue: English
Weight: 208 KB
Volume: 127
Category: Article
ISSN: 0002-7863
DOI: 10.1021/ja055710p

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## 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.