A Chemoenzymatic Route to the (+)-Form of the Amaryllidaceae Alkaloid Narseronine

Abstract

The enzymatically derived and enantiopure cis-1,2-dihydrocatechol 1 has been converted, over 14 one-pot operations, into the (+)-form of the alkaloid narseronine (2). The present study, which complements earlier work that established a route from metabolite 1 to enantiomer (–)-2, involves an N-bromosuccinimide/tri-n-butyltin hydride-mediated cyclisation reaction to construct the unsaturated B-ring lactone of the target compound.