99221-24-6Relevant articles and documents
Asymmetric synthesis of the protoberberine alkaloid (s)-(-)-xylopinine using enantiopure sulfinimines
Davis, Franklin A.,Mohanty, Pradyumna K.
, p. 1290 - 1296 (2002)
A concise enantioselective synthesis of (S)-(-)-xylopinine (1) is described involving the addition of the laterally lithiated derivative of o-tolunitrile of 16 to enantiopure sulfinimine (+)-14. Treatment of the resulting cyano sulfinamide adduct (-)-17b with DIBAL-H accomplishes five operations in a single pot and furnishes the cyclic imine (+)-18 in good yield. Reduction and cyclization affords (S)-(-)-1. Alternatively basic hydrolysis of 17b,c gives isoquinolone 21 that is cyclized and reduced to give (S)-(-)-1.