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Stereospecific C-H activation as a key step for asymmetric synthesis of various biologically active cyclopropanes

Abstract

A rapid and efficient synthesis of hoshinolatame, enantiopure cyclopropane containing natural product is described. This strategy is based on stereospecific C(sp3)-H activation allowing unprecedented olefination on the cyclopropane core. Use of originally developped by our group stereogenic and easily recyclable directing group (S)-2-(p-tolylsulfinyl)aniline (APS), allows obtention of diastereomerically pure products in high yields. Optically pure cyclopropanes are subsequently converted into enantiomerically pure targeted natural product. Furthermore a closely related synthetic scenario is employed to build up precursors of grenadamide and cascarillic acid.

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Publication details

The article was accepted on 15 Sep 2017 and first published on 19 Sep 2017


Article type: Research Article
DOI: 10.1039/C7QO00737J
Citation: Org. Chem. Front., 2017, Accepted Manuscript
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    Stereospecific C-H activation as a key step for asymmetric synthesis of various biologically active cyclopropanes

    S. Jerhaoui, P. Poutrel, J. Djukic, J. Wencel-Delord and F. Colobert, Org. Chem. Front., 2017, Accepted Manuscript , DOI: 10.1039/C7QO00737J

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