Pictet-Spengler reaction of biogenic amines with (2R)-N-glyoxyloylbornane-10,2-sultam. Enantioselective synthesis of (S)-(+)-N-methylcalycotomine

Article abstract of DOI:10.1016/0957-4166(95)00380-0

(2R)-N-glyoxyloylbornane-10,2-sultam reacted with dopamine hydrochloride, forming the Pictet-Spengler condensation product, which was further converted into (S)-(+)-N-methylcalycotomine of high enantiomeric purity. The same kind of reaction with tryptamine hydrochloride gave the condensation product with 100% d.e.