Concise enantioselective synthesis of 3,5-dialkyl-substituted indolizidine alkaloids via sequential cross-metathesis-double-reductive cyclization |
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Authors: | Randl Stefan Blechert Siegfried |
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Institution: | Technische Universit?t Berlin, Institut für Chemie, Strasse des 17. Juni 135, D-10623 Berlin, Germany. |
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Abstract: | An efficient stereoselective synthesis of two 3,5-dialkyl-substituted indolizidine alkaloids is reported. The convergent syntheses are based on a novel sequence of a cross-metathesis (CM) reaction of an alpha,beta-unsaturated ketone and a chiral homoallylic amine followed by a domino reaction involving hydrogenation, N-deprotection, and two diastereoselective reductive aminations. Our concept presents one of a few examples of a highly selective CM reaction in the synthesis of a natural product. |
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