Mersiphyllines A and B from Kopsia. Determination of relative configuration at a quaternary center via formation of an alkaloid–borane complex

Two new pentacyclic alkaloids, mersiphyllines A (1) and B (2), belonging to the novel mersinine group, and incorporating carboxylic acid functionalities on a quaternary center, were isolated from Kopsia singapurensis. The structures were determined by spectroscopic analysis. Determination of the relative configuration at the quaternary center bearing the acid function was facilitated by the formation of an alkaloid–borane complex. The structure of 1 was also confirmed by X-ray diffraction analysis.