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Enantioselective synthesis of the carbacephem antibiotic loracarbef via Mitsunobu and Dieckmann cyclization from an unnatural amino acid

✍ Scribed by Jerry W Misner; Jack W Fisher; John P Gardner; Steve W Pedersen; Kristina L Trinkle; Billy G Jackson; Tony Y Zhang

Publisher: Elsevier Science
Year: 2003
Tongue: French
Weight: 180 KB
Volume: 44
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(03)01483-7

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✦ Synopsis

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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