213825-82-2Relevant academic research and scientific papers
Dioxirane epoxidation of 10-membered-ring stilbene lactams as synthetic precursors to protoberberines
Rodriguez, Gema,Castedo, Luis,Dominguez, Domingo,Saa, Carlos,Adam, Waldemar,Saha-Moeller, Chantu R.
, p. 877 - 883 (2007/10/03)
Silylated stilbene lactams 1, prepared by intramolecular addition of an aryl radical to a trimethylsilylacetylene, were converted into protoberberines by dimethyldioxirane (DMD) epoxidation and subsequent acid- catalyzed cyclization of the epoxysilane with HCl. Treatment of the nonsilylated trans- and cis-stilbene derivatives with DMD afforded 13- hydroxytetrahydroprotoberberines and 13a-hydroxy-13- ketotetrahydroprotoberberines as the main products. Tetrahydroprotoberberines were also obtained in excellent yields by the reaction of both silylated and nonsilylated lactams with hydriodic acid.
