A methodological study towards the total synthesis of marmycin A/B is described exploiting a commercial anthraquinone molecule as model compound. The challenging synthetic pathway uncovers a copper-catalysed Ullmann cross-coupling to attach the sugar backbone by means of C–N bond formation and, finally, an intramolecular Friedel–Crafts C–C glycosylation to successfully afford the core structure of marmycin A. This methodology has been successfully applied to the genuine anthraquinone moiety leading to the natural product and simpler structural analogues

A Synthetic Study towards the Marmycins and Analogues / Cañeque, Tatiana; Gomes, Filipe; Mai, Trang; Blanchard, Florent; Retailleau, Pascal; Gallard, Jean François; Maestri, Giovanni; Malacria, Max; Rodriguez, Raphaël. - In: SYNTHESIS. - ISSN 0039-7881. - 49:(2017), pp. 587-592. [10.1055/s-0035-1562627]

A Synthetic Study towards the Marmycins and Analogues

MAESTRI, Giovanni;
2017-01-01

Abstract

A methodological study towards the total synthesis of marmycin A/B is described exploiting a commercial anthraquinone molecule as model compound. The challenging synthetic pathway uncovers a copper-catalysed Ullmann cross-coupling to attach the sugar backbone by means of C–N bond formation and, finally, an intramolecular Friedel–Crafts C–C glycosylation to successfully afford the core structure of marmycin A. This methodology has been successfully applied to the genuine anthraquinone moiety leading to the natural product and simpler structural analogues
2017
A Synthetic Study towards the Marmycins and Analogues / Cañeque, Tatiana; Gomes, Filipe; Mai, Trang; Blanchard, Florent; Retailleau, Pascal; Gallard, Jean François; Maestri, Giovanni; Malacria, Max; Rodriguez, Raphaël. - In: SYNTHESIS. - ISSN 0039-7881. - 49:(2017), pp. 587-592. [10.1055/s-0035-1562627]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11381/2812217
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