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Title
Total Synthesis of (−)-Crinine. Use of Tandem Cationic Aza- Cope Rearrangement/ Mannich Cyclizations for the Synthesis of Enantiomerically Pure Amaryllidaceae Alkaloids.
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 AgNO3 at 25°C to give cis-perhydroindolone 8 in 81% yield.