Expedient Synthesis of (+)‐Lycopalhine A |
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| Authors: | Benjamin M. Williams Prof. Dr. Dirk Trauner |
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| Affiliation: | Department of Chemistry, Ludwig-Maximilians-Universit?t München, Munich, Germany |
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| Abstract: | Two amino acids play a key role in the first total synthesis of lycopalhine A. l ‐glutamic acid serves as a convenient chiral starting material for the 13‐step synthesis, and l ‐proline promotes an unusual 5‐endo‐trig Mannich cyclization that generates the central pyrrolidine ring of the Lycopodium alkaloid. The bicyclo[3.3.0]octanol moiety of the molecule is formed through an intramolecular aldol addition that may occur spontaneously in nature. |
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| Keywords: | aldol reaction amino acids Lycopodium alkaloids Mannich reaction total synthesis |
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