Application of the 2-Azaallyl Anion Cycloaddition Method to Syntheses of (+/-)-Crinine and (+/-)-6-Epicrinine

Article abstract of DOI:10.1016/0040-4039(94)88457-9

Transmetalation of the (2-azaallyl)stannane 9 with n-BuLi produced the 2-azaallyl anion 12 which undervent an intramolecular cycloaddition with an alkene to give the perhydroindole 10 in 80percent yield as a single stereoisomer.Transformation of 10 to 6-epicrinine 2 and crinine 1 was readily accomplished.