Investigations into Simplified Analogues of the Herbicidal Natural Product (+)‐Cornexistin

Author:

Steinborn Christian1,Tancredi Aldo1,Habiger Christoph1,Diederich Christina2ORCID,Kramer Jan2,Reingruber Anna M.2,Laber Bernd2,Freigang Jörg3,Lange Gudrun2,Schmutzler Dirk2,Machettira Anu2,Besong Gilbert2,Magauer Thomas1ORCID,Barber David M.2ORCID

Affiliation:

1. Institute of Organic Chemistry and Center for Molecular Biosciences University of Innsbruck Innrain 80–82 6020 Innsbruck Austria

2. Research & Development, Weed Control Bayer AG, Crop Science Division Industriepark Höchst 65926 Frankfurt am Main Germany

3. Research & Development, Hit Discovery Bayer AG, Crop Science Division Alfred-Nobel-Straße 50 40789 Monheim am Rhein Germany

Abstract

AbstractWe report the design, synthesis and biological evaluation of simplified analogues of the herbicidal natural product (+)‐cornexistin. Guided by an X‐Ray co‐crystal structure of cornexistin bound to transketolase from Zea mays, we attempted to identify the key interactions that are necessary for cornexistin to maintain its herbicidal profile. This resulted in the preparation of three novel analogues investigating the importance of substituents that are located on the nine‐membered ring of cornexistin. One analogue maintained a good level of biological activity and could provide researchers insights in how to further optimize the structure of cornexistin for commercialization in the future.

Funder

Austrian Science Fund

Publisher

Wiley

Subject

General Chemistry,Catalysis,Organic Chemistry

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