Enantioselective synthesis of the carbacephem antibiotic loracarbef via Mitsunobu and Dieckmann cyclization from an unnatural amino acid |
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| Authors: | Jerry W MisnerJack W Fisher John P GardnerSteve W Pedersen Kristina L TrinkleBilly G Jackson Tony Y Zhang |
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| Institution: | Chemical Process Research and Development, Lilly Research Laboratories, A Division of Eli Lilly and Company, Indianapolis, IN 46285-4813, USA |
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| Abstract: | The nucleus of the carbacephem antibiotic loracarbef was synthesized in a highly efficient and enantioselective fashion from 2S,3S-2-amino-3-hydroxy-6-heptenoic acid (AHHA), which was derived from enzyme-catalyzed condensation of glycine and 4-pentenaldehyde. The bicyclic framework of this compound was established through sequential Mitsunobu reaction and aldol condensations. |
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