114127-64-9Relevant articles and documents
Complete Stereocontrol in the Synthesis of Harmonine and Novel Analogues Facilitated by a Grubbs Z-Selective Cross-Metathesis Catalyst
Abel, Steven-Alan G.,Olivier, Wesley J.,Pederson, Richard L.,Bissember, Alex C.,Smith, Jason A.
, p. 1815 - 1820 (2015/12/26)
(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.