Complete Stereocontrol in the Synthesis of Harmonine and Novel Analogues Facilitated by a Grubbs Z-Selective Cross-Metathesis Catalyst

Article abstract of DOI:10.1071/CH15397

(R)-Harmonine was synthesised in 15% overall yield via a six-step sequence exploiting a Z-selective cross-metathesis reaction as its centrepiece. By this strategy, the cis-olefin present in the target could be installed exclusively. The use of an alcohol and an ester as the amine precursors was crucial for isolating the cross-metathesis product from the self-metathesis products. This method was also used to prepare two novel analogues of harmonine.