Synthesis of (+)- and (–)-scoulerine and of (+)- and (–)-coreximine

Abstract

Three routes for the synthesis of scoulerine (as II) are described. Two of these employ the Bischler–Napieralski reaction. In the third, norreticuline (as XX) is resolved, and the (+)- and (–)-enantiomers are used for synthesis of the optically active forms of scoulerine and coreximine (as XXII). The absolute configuration of scoulerine is related chemically to that of the natural amino-acids.