Journal
COMBINATORIAL CHEMISTRY & HIGH THROUGHPUT SCREENING
Volume 8, Issue 7, Pages 607-615Publisher
BENTHAM SCIENCE PUBL LTD
DOI: 10.2174/138620705774575373
Keywords
natural product-like; agrochemical; herbicide; ortho-quinone; intramolecular cycloaddition; Diels-Alder; bicyclo[2,2,2]octenone
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A general route to a series of differentially substituted bicyclo[2,2,2]octenones has been developed, making use of the in situ intramolecular Diels Alder reaction of masked ortho-benzoquinones. This approach was used to synthesize a series of thirteen key acid-containing templates from which a solution phase discovery library of 1126 diverse amides was then constructed. The rigid polycyclic nature of the templates and the prevalence of oxygenated functionality confer natural product-like qualities and three-dimensional diversity. The library was screened in FITS in vivo against a number of weed, insect and fungal model organisms leading to the discovery of a novel series of herbicidally active compounds. The development, production and biological activity of the library are described.
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