122480-73-3Relevant academic research and scientific papers
INVERSION OF A HYDROXYL GROUP BY THE NEIGHBORING-GROUP PARTICIPATION OF A URETHANE--A GENERAL AND STERESELECTIVE SYNTHESIS OF (+/-)-RADDEANONE, (+/-)-YENHUSOMIDINE, AND RELATED SPIROBENZYLISOQUINOLINE ALKALOIDS
Hanaoka, Miyoji,Kohzu, Masumi,Yasuda, Shingo
, p. 4248 - 4251 (2007/10/02)
(+/-)-Raddeanone (1) was stereoselectively synthesized from the corresponding protoberberine (5) via the ketal (17) in four steps.Inversion of a hydroxyl group in the ketal (17) was realized by the neighboring-group participation of a urethane to afford the diastereomeric ketal (22), which was easily converted to (+/-)-yenhusomidine (3).These alkaloids (1 and 3) were converted to (+/-)-raddeanine (18), (+)-raddeanidine (20), and (+/-)-yenhusomine (25).KEYWORDS--spirobenzylisoquinoline alkaloid; protoberberine; raddeanone; yenhusomidine; raddeanine; raddeanidine; yenhusomine; neighboring-group participation; urethane
