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Issue 28, 2015
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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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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.

Graphical abstract: 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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Publication details

The article was received on 02 May 2015, accepted on 09 Jun 2015 and first published on 09 Jun 2015


Article type: Paper
DOI: 10.1039/C5OB00890E
Citation: Org. Biomol. Chem., 2015,13, 7655-7663
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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

    S. Coe, N. Pereira, J. V. Geden, G. J. Clarkson, D. J. Fox, R. M. Napier, P. Neve and M. Shipman, Org. Biomol. Chem., 2015, 13, 7655
    DOI: 10.1039/C5OB00890E

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