Enantioselective synthesis of (−)-barrenazines A and B |
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Authors: | M Montserrat Martínez José Pérez Sestelo |
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Institution: | Departamento de Química Fundamental, Universidade da Coruña, E-15071 A Coruña, Spain |
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Abstract: | A short enantioselective synthesis of barrenazines A and B is described. Barrenazines A and B are prepared following a common synthetic route in nine steps (19% overall yield) and eight steps (21% overall yield), respectively, from readily available 4-methoxy-3-(triisopropylsilyl)pyridine. The synthesis relies on a highly diastereoselective nucleophilic addition of a Grignard reagent to a chiral acylpyridinium salt, a radical azidation of a silyl enol ether and the assembly of the pyrazine ring by reductive dimerization of a functionalized 5-azidopiperidin-4-one. |
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Keywords: | Natural product synthesis Stereoselective synthesis Acylpyridinium salts Azides Pyrazines |
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