Cornexistin
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| Category | Others |
| Catalog number | BBF-01061 |
| CAS | 123068-35-9 |
| Molecular Weight | 308.33 |
| Molecular Formula | C16H20O6 |
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Description
It is produced by the strain of Paecilomyces variotii SANK 21086. It has the activity of removing annual weeds (0.5 kg/he) and has no antibacterial effect.
Specification
| Synonyms | 14-Dihydroxycornestin; (4R,5S,8S,9Z)-9-ethylidene-5,8-dihydroxy-4-propyl-4,5,7,8,9,10-hexahydro-1H-cyclonona[c]furan-1,3,6-trione |
| IUPAC Name | (4R,5S,8S,9Z)-9-ethylidene-5,8-dihydroxy-4-propyl-5,7,8,10-tetrahydro-4H-cyclonona[c]furan-1,3,6-trione |
| Canonical SMILES | CCCC1C(C(=O)CC(C(=CC)CC2=C1C(=O)OC2=O)O)O |
| InChI | InChI=1S/C16H20O6/c1-3-5-9-13-10(15(20)22-16(13)21)6-8(4-2)11(17)7-12(18)14(9)19/h4,9,11,14,17,19H,3,5-7H2,1-2H3/b8-4-/t9-,11+,14+/m1/s1 |
| InChI Key | ILMHTGUGRLGMCR-LRIVTRFWSA-N |
Properties
| Appearance | Acicular Crystal |
| Melting Point | 100-103 °C |
| Solubility | Soluble in Methanol |
Reference Reading
1. Evolution of a Strategy for the Total Synthesis of (+)-Cornexistin
Raphael E Wildermuth, Christian Steinborn, David M Barber, Kim S Mühlfenzl, Mario Kendlbacher, Peter Mayer, Klaus Wurst, Thomas Magauer Chemistry. 2021 Aug 19;27(47):12181-12189. doi: 10.1002/chem.202101849. Epub 2021 Jul 7.
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 or Nozaki-Hiyama-Kishi (NHK) reaction. Those strategies suffered from low yields and were jeopardized by a late-stage installation of the Z-alkene, as well as the stereocenters along the eastern periphery. These issues were addressed by employing a chiral-pool strategy that involved construction of the crucial stereocenters at C2, C3 and C8 at an early stage with installation of the maleic anhydride as late as possible. The successful approach featured an intermolecular NHK coupling to install the Z-alkene, a syn-Evans-aldol reaction to forge the stereocenters along the eastern periphery, an intramolecular allylic alkylation to close the nine-membered carbocycle, and a challenging stepwise hydrolysis of a β-keto nitrile to furnish the maleic anhydride.
2. Investigations into Simplified Analogues of the Herbicidal Natural Product (+)-Cornexistin
Christian Steinborn, Aldo Tancredi, Christoph Habiger, Christina Diederich, Jan Kramer, Anna Reingruber, Bernd Laber, Jörg Freigang, Gudrun Lange, Dirk Schmutzler, Anu Machettira, Gilbert Besong, Thomas Magauer, David M Barber Chemistry. 2023 Feb 20;e202300199. doi: 10.1002/chem.202300199. Online ahead of print.
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 the transketolase enzyme 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.
3. Total Synthesis of (+)-Cornexistin
Christian Steinborn, Raphael E Wildermuth, David M Barber, Thomas Magauer Angew Chem Int Ed Engl. 2020 Sep 21;59(39):17282-17285. doi: 10.1002/anie.202008158. Epub 2020 Aug 18.
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 intramolecular alkylation to form the nine-membered carbocycle. The delicate maleic anhydride moiety of the nonadride skeleton was constructed from a β-keto nitrile. The developed route enabled the synthesis of 165 mg (+)-cornexistin.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
