Total synthesis of (-)-alpha-kainic acid by (-)-sparteine-mediated asymmetric deprotonation-cycloalkylation |
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Authors: | Martinez M Montserrat Hoppe Dieter |
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Institution: | Organisch-Chemisches Institut, Westf?lische Wilhelms-Universit?t Münster, Corrensstrasse 40, D-48149 Münster, Germany. |
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Abstract: | reaction: see text] We report a new enantioselective synthesis of (-)-alpha-kainic acid from d-serine methyl ester hydrochloride, based on a (-)-sparteine-mediated asymmetric deprotonation of an intermediate carbamate that, by stereospecific anti S(N)'S(E)' intramolecular cycloalkylation, leads to the pyrrolidine ring precursor of (-)-alpha-kainic acid, in high yield and diastereoselectivity. The intermediate pyrrolidine was further transformed to (-)-alpha-kainic acid in three steps. |
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