Stereoselective syntheses of polyhydroxylated azepane derivatives from sugar-based epoxyamides. Part 1: synthesis from d-mannose |
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| Authors: | Noe Oña Antonio Romero Carmen Assiego Claudia Bello Pierre Vogel M. Soledad Pino-González |
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| Affiliation: | 1. Departamento de Química Orgánica, Facultad de Ciencias. Universidad de Málaga, 29071 Málaga, Spain;2. Laboratory of Glycochemistry and Asymmetric Synthesis, Ecole Polytechnique Fédérale (EPFL) Batochime CH-1015, Lausanne, Switzerland |
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| Abstract: | An approach to the synthesis of polyhydroxyazepane derivatives from sugar-based epoxyamides or epoxyalcohols, in which the total regioselective epoxide opening by nitrogen nucleophiles is the key step, is described. Thus, novel polyhydroxyazepane carboxamides and aminomethyl polyhydroxyazepanes, with potential pharmacological interest, are synthesized from diacetone d-mannose. Configurational assignments of the obtained products were determined. |
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