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Complete stereocontrol in the synthesis of harmonine and novel analogues facilitated by a Grubbs Z-selective cross-metathesis catalysis
journal contribution
posted on 2023-05-18, 15:35 authored by Steven Abel, Wesley Olivier, Pederson, RL, Alexander BissemberAlexander Bissember, Jason SmithJason Smith(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.
History
Publication title
Australian Journal of ChemistryVolume
68Issue
12Pagination
1815-1820ISSN
0004-9425Department/School
School of Natural SciencesPublisher
CSIRO PublishingPlace of publication
150 Oxford St, Po Box 1139, Collingwood, Australia, Victoria, 3066Rights statement
Copyright CSIRO 2015Repository Status
- Restricted