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

Article abstract of DOI:10.1002/hlca.19850680324

The total synthesis of enantiomerically pure (-)-crinine (1) in 10 steps and 6percent overall yield from cyclopentene oxide is reported.The key step was the rearrangement of 7 upon reaction with AgNO3 at 25 deg C to give cis-perhydroindolone 8 in 81 perce