Michael. (2015) Ring closing metathesis reactions of α-methylene-β-lactams : application to the synthesis of a simplified phyllostictine analogue with herbicidal activity. Organic & Biomolecular Chemistry, Volume 13 (Number 28). pp. 7655-7663. Permanent WRAP url:http://wrap.warwick.ac.uk/70250 Copyright and reuse:The Warwick Research Archive Portal (WRAP) makes this work by researchers of the University of Warwick available open access under the following conditions. Copyright © and all moral rights to the version of the paper presented here belong to the individual author(s) and/or other copyright owners. To the extent reasonable and practicable the material made available in WRAP has been checked for eligibility before being made available.Copies of full items can be used for personal research or study, educational, or not-forprofit purposes without prior permission or charge. Provided that the authors, title and full bibliographic details are credited, a hyperlink and/or URL is given for the original metadata page and the content is not changed in any way. Ring closing metathesis (RCM) reactions of -methylene--lactams are used to construct strained 11-and 12-membered macrocycles that mimic key structural elements of phyllostictine A. The highest yield and stereoselectivity was achieved making 12-membered macrocycle Z-19 with use of a p-methoxyphenyl group on the lactam nitrogen. Interestingly, substrate concentration had an important influence on the stereochemical course of the reaction. A simplified analogue produced using this approach displays phytotoxic activity against Chlamydomonas reinhardtii suggesting that the -methylene--lactam subunit is responsible, at least in part, for the herbicidal activity of phyllostictine A .
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