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Complete stereocontrol in the synthesis of harmonine and novel analogues facilitated by a Grubbs Z-selective cross-metathesis catalysis

Citation

Abel, S-AG and Olivier, WJ and Pederson, RL and Bissember, AC and Smith, JA, Complete stereocontrol in the synthesis of harmonine and novel analogues facilitated by a Grubbs Z-selective cross-metathesis catalysis, Australian Journal of Chemistry, 68, (12) pp. 1815-1820. ISSN 0004-9425 (2015) [Refereed Article]

Copyright Statement

Copyright CSIRO 2015

DOI: doi:10.1071/CH15397

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.

Item Details

Item Type:Refereed Article
Keywords:catalysis, cross-metathesis, harmonine, insect hormones, Harlequin ladybird
Research Division:Chemical Sciences
Research Group:Organic Chemistry
Research Field:Organic Chemical Synthesis
Objective Division:Expanding Knowledge
Objective Group:Expanding Knowledge
Objective Field:Expanding Knowledge in the Chemical Sciences
Author:Abel, S-AG (Mr Steve Abel)
Author:Olivier, WJ (Mr Wesley Olivier)
Author:Bissember, AC (Dr Alex Bissember)
Author:Smith, JA (Associate Professor Jason Smith)
ID Code:105589
Year Published:2015
Web of Science® Times Cited:1
Deposited By:Chemistry
Deposited On:2016-01-08
Last Modified:2016-05-18
Downloads:0

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