The Plakotenins: Biomimetic Diels–Alder Reactions,Total Synthesis,Structural Investigations,and Chemical Biology |
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| Authors: | Dr. Emmanuel Bourcet Larissa Kaufmann Dr. Stephanie Arzt Dr. Angela Bihlmeier Prof. Dr. Wim Klopper Dr. Ute Schepers Prof. Dr. Stefan Bräse |
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| Affiliation: | 1. Institute of Organic Chemistry and Center for Functional Nanostructures (CFN), Karlsruhe Institute of Technology (KIT), Campus South, Fritz‐Haber‐Weg 6, 76131 Karlsruhe (Germany), Fax: (+49)?721‐608‐48581;2. Institute of Toxicology and Genetics, Karlsruhe Institute of Technology (KIT), Campus North, Hermann‐von‐Helmholtz‐Platz 1, 76344 Eggenstein‐Leopoldshafen (Germany);3. Institute of Physical Chemistry and Center for Functional Nanostructures (CFN), Karlsruhe Institute of Technology (KIT), Campus South, Fritz‐Haber‐Weg 2, 76131 Karlsruhe (Germany) |
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| Abstract: | The total synthesis of plakotenin, a cytotoxic marine natural product, using a biomimetic Diels–Alder reaction is described in detail. Two approaches were used, whereby the Diels–Alder reaction occurs at different stages of the synthesis. Homo‐ and nor‐plakotenin, related natural products, were also prepared, as well as iso‐plakotenin, a diastereoisomer of plakotenin. The syntheses prove the relative and absolute stereochemistry of the latter. The chemical biology of the plakotenins was investigated on selected compounds. |
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| Keywords: | biomimetic synthesis chemical biology cycloaddition natural products polyketides |
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