Complete Stereocontrol in the Synthesis of Harmonine and Novel Analogues Facilitated by a Grubbs Z-Selective Cross-Metathesis Catalyst
Steven-Alan G. Abel A , Wesley J. Olivier A , Richard L. Pederson B , Alex C. Bissember A C and Jason A. Smith A C
+ Author Affiliations
- Author Affiliations
A School of Physical Sciences – Chemistry, University of Tasmania, Hobart, Tas. 7001, Australia.
B Materia Inc., 60 N. San Gabriel Boulevard, Pasadena, CA 91107, USA.
C Corresponding authors. Email: alex.bissember@utas.edu.au; jason.smith@utas.edu.au
Australian Journal of Chemistry 68(12) 1815-1820 https://doi.org/10.1071/CH15397
Submitted: 2 July 2015 Accepted: 4 August 2015 Published: 3 September 2015
Abstract
(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.
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