Resolution of prenyl bromohydrin esters and derivatives: synthesis of the quinoline alkaloid (+)-(R)- and (−)-(S)- lunacridine

Abstract Chromatographic separation of the bromohydrin MTPA diastereoisomers formed at the prenyl group attached to quinoline and coumarin rings is reported; base catalysed cyclization of the bromo MTPA esters in the quinoline series yielded the corresponding prenyl epoxide enantiomers. This provides a synthetic route to the enantiopure quinoline alkaloid lunacridine 11 and to the dihydrofuroquinoline 8-methoxy-platydesmine 8 .