Title: Synthesis and agrochemical screening of a library of natural product-like bicyclo[2,2,2]octenones
Volume: 8
Issue: 7
Author(s): Stephen C. Smith, Donald R. James, Matthew M. Abelman and Graham J. Sexton
Affiliation:
Keywords:
natural product-like, agrochemical, herbicide, ortho-quinone, intramolecular cycloaddition, diels-alder, bicyclo[2,2,2]octenone
Abstract: 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 HTS 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.
