A totally stereocontrolled route to N-methyl-γ-amino-β-hydroxy acids: Asymmetric synthesis of the amino acid component of hapalosin |
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Authors: | M nica Catasú s, Albert Moyano, Miquel A Peric s,Antoni Riera |
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Affiliation: | aUnitat de Recerca en Síntesi Asimètrica, Departament de Quḿica Orgànica, Universitat de Barcelona, c/ Martí i Franquès, 1-11 08028-Barcelona, Spain |
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Abstract: | A new approach to the synthesis of N-methyl-γ-amino-β-hydroxy acids, compounds that are essential components of several depsipeptides exhibiting highly interesting therapeutic profiles, is presented. Relevant steps in the synthetic sequence involve the totally stereoselective preparation of a protected aminoalkyl epoxide from a highly enantiopure 2,3-epoxy alcohol, efficient N-methylation and three-step conversion to the desired N-methyl amino acid. The method is exemplified by the enantioselective synthesis of (3R,4S)-4-(N-methylamino)-3-hydroxy-5-phenylpentanoic acid in two differently protected forms. |
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Keywords: | Amino alcohols antitumour compounds asymmetric synthesis depsipeptides epoxides |
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