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Total Synthesis of (+)-Cornexistin |
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| Authors: | Christian Steinborn Dr Raphael E Wildermuth Dr David M Barber Prof Dr Thomas Magauer |
| Institution: | 1. Institute of Organic Chemistry and Center for Molecular Biosciences, Leopold-Franzens-University Innsbruck, Innrain 80–82, 6020 Innsbruck, Austria
These authors contributed equally to this work.;2. Research and Early Development, Respiratory & Immunology, AstraZeneca, 43183 Mölndal, Sweden These authors contributed equally to this work.;3. Research & Development, Weed Control Chemistry, Bayer AG, Crop Science Division, Industriepark Höchst, 65926 Frankfurt am Main, Germany;4. Institute of Organic Chemistry and Center for Molecular Biosciences, Leopold-Franzens-University Innsbruck, Innrain 80–82, 6020 Innsbruck, Austria |
| Abstract: | 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. |
| Keywords: | herbicides carbocycles natural products nonadride total synthesis |