Enantiospecific total synthesis of the enantiomer of the indole alkaloid affinisine

Abstract The enantiomer of affinisine has been synthesized (from l -tryptophan) with 100% diastereoselectivity via the asymmetric Pictet–Spengler reaction coupled with a Pd 0 (enolate mediated) coupling process. This enantiomer has also been converted into a key intermediate which provides a route to the enantiomers of both macroline and alstonerine following the previous work of LeQuesne.