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Total Synthesis of (+)-Cornexistin.
Steinborn C, Wildermuth RE, Barber DM, Magauer T. Steinborn C, et al. Angew Chem Int Ed Engl. 2020 Sep 21;59(39):17282-17285. doi: 10.1002/anie.202008158. Epub 2020 Aug 18. Angew Chem Int Ed Engl. 2020. PMID: 32558114 Free PMC article.
Herein, we describe the first total synthesis of (+)-cornexistin as well as its 8-epi-isomer starting from malic acid. The robust and scalable route features a Nozaki-Hiyama-Kishi reaction, an auxiliary-controlled syn-Evans-aldol reaction, and a highly efficient intramolec …
Herein, we describe the first total synthesis of (+)-cornexistin as well as its 8-epi-isomer starting from malic acid. The robust and …
Evolution of a Strategy for the Total Synthesis of (+)-Cornexistin.
Wildermuth RE, Steinborn C, Barber DM, Mühlfenzl KS, Kendlbacher M, Mayer P, Wurst K, Magauer T. Wildermuth RE, et al. Chemistry. 2021 Aug 19;27(47):12181-12189. doi: 10.1002/chem.202101849. Epub 2021 Jul 7. Chemistry. 2021. PMID: 34105834 Free PMC article.
Herein is given a full account of the evolution of the first total synthesis of (+)-cornexistin. Initial efforts were based on masking the reactive maleic anhydride moiety as a 3,4-substituted furan and on forming the nine-membered carbocycle in an intramolecular Conia-ene …
Herein is given a full account of the evolution of the first total synthesis of (+)-cornexistin. Initial efforts were based on maskin …
Investigations into Simplified Analogues of the Herbicidal Natural Product (+)-Cornexistin.
Steinborn C, Tancredi A, Habiger C, Diederich C, Kramer J, Reingruber AM, Laber B, Freigang J, Lange G, Schmutzler D, Machettira A, Besong G, Magauer T, Barber DM. Steinborn C, et al. Chemistry. 2023 Jul 11;29(39):e202300199. doi: 10.1002/chem.202300199. Epub 2023 May 23. Chemistry. 2023. PMID: 36807428 Free PMC article.
We 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 interac …
We report the design, synthesis and biological evaluation of simplified analogues of the herbicidal natural product (+)-cornexistin. …
Genetic and chemical characterisation of the cornexistin pathway provides further insight into maleidride biosynthesis.
Williams K, Szwalbe AJ, Dickson C, Desson TR, Mulholland NP, Vincent JL, Clough JM, Bailey AM, Butts CP, Willis CL, Simpson TJ, Cox RJ. Williams K, et al. Chem Commun (Camb). 2017 Jul 11;53(56):7965-7968. doi: 10.1039/c7cc03303f. Chem Commun (Camb). 2017. PMID: 28660939
The biosynthesis of the herbicide cornexistin in the fungus Paecilomyces variotii was investigated by full sequencing of its genome, knockout of key genes within its biosynthetic gene cluster and isolation and identification of intermediate compounds. ...
The biosynthesis of the herbicide cornexistin in the fungus Paecilomyces variotii was investigated by full sequencing of its genome, …
Cornexistin: a new fungal metabolite with herbicidal activity.
Nakajima M, Itoi K, Takamatsu Y, Sato S, Furukawa Y, Furuya K, Honma T, Kadotani J, Kozasa M, Haneishi T. Nakajima M, et al. J Antibiot (Tokyo). 1991 Oct;44(10):1065-72. doi: 10.7164/antibiotics.44.1065. J Antibiot (Tokyo). 1991. PMID: 1955388 Free article.
Cornexistin, a new compound demonstrating promising herbicidal activity, was purified from the culture filtrate of a newly-isolated fungus identified as Paecilomyces variotii SANK 21086. ...Chemical structure elucidation was conducted by analyses of various spectral data a …
Cornexistin, a new compound demonstrating promising herbicidal activity, was purified from the culture filtrate of a newly-isolated f …
Synthesis of the Core Framework of the Cornexistins by Intramolecular Nozaki-Hiyama-Kishi Coupling.
Aimon A, Farrugia LJ, Clark JS. Aimon A, et al. Molecules. 2019 Jul 22;24(14):2654. doi: 10.3390/molecules24142654. Molecules. 2019. PMID: 31336669 Free PMC article.
A new and direct approach to the construction of the core framework of the herbicidal natural products cornexistin and hydroxycornexistin has been developed. Formation of the nine-membered carbocycle found in the natural products has been accomplished by an intramolecular …
A new and direct approach to the construction of the core framework of the herbicidal natural products cornexistin and hydroxycornexi …
Synthesis of the carbocyclic core of the cornexistins by ring-closing metathesis.
Clark JS, Marlin F, Nay B, Wilson C. Clark JS, et al. Org Lett. 2003 Jan 9;5(1):89-92. doi: 10.1021/ol027265y. Org Lett. 2003. PMID: 12509898
An advanced intermediate in the synthesis of the phytotoxins cornexistin and hydroxycornexistin has been synthesized. Sequential palladium-mediated sp(2)-sp(3) fragment coupling and ring-closing diene metathesis have been used to construct the nine-membered carbocyclic cor …
An advanced intermediate in the synthesis of the phytotoxins cornexistin and hydroxycornexistin has been synthesized. Sequential pall …