A Simple BF3•Et2O-mediated Cycloaddition Reaction to the Formation of Cyclic Monoterpenoid Pyrano[3,2-a]carbazole Alkaloids

Abstract

A Lewis acid BF3•Et2O-mediated intramolecular cycloaddition reaction of mahanimbine (1) is described. Three cycloadducts, bicyclomahanimbine (2), cyclomahanimbine (3) and murrayazolinine (4) were obtained. The structural characterization of these compounds was determined by 1D and 2D NMR experiments. These compounds showed no cytotoxic activity against human MRC-5 cells (IC50 > 60 μg/mL). Compound 3 showed the highest inhibition cytotoxic effects against HeLa and HL-60 cancer cells with IC50 values of 10.0 and 28.7 μg/mL, respectively. This strategy opens a new approach for the synthesis of biologically significant cyclic monoterpenoid pyrano[3,2-a]carbazole alkaloids.