Stereospecific C-H activation as a key step for the asymmetric synthesis of various biologically active cyclopropanes
| Autor: | Soufyan Jerhaoui, Françoise Colobert, P. Poutrel, Joanna Wencel-Delord, Jean-Pierre Djukic |
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| Přispěvatelé: | Laboratoire d'innovation moléculaire et applications (LIMA), Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie de Strasbourg, Centre National de la Recherche Scientifique (CNRS)-Université Louis Pasteur - Strasbourg I-Institut de Chimie du CNRS (INC), Laboratoire de Chimie Quantique, Centre National de la Recherche Scientifique (CNRS), Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC) |
| Jazyk: | angličtina |
| Rok vydání: | 2018 |
| Předmět: |
Natural product
010405 organic chemistry Stereochemistry [CHIM.ORGA]Chemical Sciences/Organic chemistry Organic Chemistry Enantioselective synthesis Biological activity 010402 general chemistry 01 natural sciences 0104 chemical sciences Stereocenter Cyclopropane chemistry.chemical_compound Aniline Stereospecificity Enantiopure drug chemistry SYNCAT |
| Zdroj: | Organic Chemistry Frontiers Organic Chemistry Frontiers, Royal Society of Chemistry, 2018, 5, pp.409-414. ⟨10.1039/C7QO00737J⟩ |
| ISSN: | 2052-4129 |
| DOI: | 10.1039/C7QO00737J |
| Popis: | A rapid and efficient synthesis of hoshinolactam, an enantiopure cyclopropane containing natural product, is described. This strategy is based on stereospecific C(sp3)–H activation via unprecedented olefination on the cyclopropane core. The use of a stereogenic and easily recyclable directing group (S)-2-(p-tolylsulfinyl)aniline (APS) which was originally developed by our group allows obtention of diastereomerically pure products in high yields. Optically pure cyclopropanes are subsequently converted into enantiomerically pure targeted natural products. Furthermore a closely related synthetic scenario is employed to build up precursors of grenadamide and cascarillic acid. |
| Databáze: | OpenAIRE |
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