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Ring closing metathesis reactions of α-methylene-β-lactams : application to the synthesis of a simplified phyllostictine analogue with herbicidal activity
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Coe, Samuel, Pereira, Nicole, Geden, Joanna V., Clarkson, Guy J., Fox, David J., Napier, R. (Richard), Neve, Paul and Shipman, 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. doi:10.1039/c5ob00890e ISSN 1477-0520.
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WRAP_0370203-ch-150715-phyllostictine_obc-2015_rev1 (1).pdf - Accepted Version - Requires a PDF viewer. Download (1248Kb) | Preview |
Official URL: http://dx.doi.org/10.1039/C5OB00890E
Abstract
Ring closing metathesis (RCM) reactions of α-methylene-β-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 α-methylene-β-lactam subunit is responsible, at least in part, for the herbicidal activity of phyllostictine A.
Item Type: | Journal Article | ||||||||
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Subjects: | Q Science > QD Chemistry | ||||||||
Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry Faculty of Science, Engineering and Medicine > Science > Life Sciences (2010- ) |
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Library of Congress Subject Headings (LCSH): | Metathesis (Chemistry), Herbicides -- Mechanism of action | ||||||||
Journal or Publication Title: | Organic & biomolecular chemistry | ||||||||
Publisher: | Royal Society of Chemistry | ||||||||
ISSN: | 1477-0520 | ||||||||
Official Date: | 28 July 2015 | ||||||||
Dates: |
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Volume: | Volume 13 | ||||||||
Number: | Number 28 | ||||||||
Number of Pages: | 9 | ||||||||
Page Range: | pp. 7655-7663 | ||||||||
DOI: | 10.1039/c5ob00890e | ||||||||
Status: | Peer Reviewed | ||||||||
Publication Status: | Published | ||||||||
Access rights to Published version: | Restricted or Subscription Access | ||||||||
Date of first compliant deposit: | 30 December 2015 | ||||||||
Date of first compliant Open Access: | 27 June 2016 | ||||||||
Funder: | Engineering and Physical Sciences Research Council (EPSRC), University of Warwick | ||||||||
Grant number: | EP/K031783/1 (EPSRC) |
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