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Updated: Jul 13, 2026

Production and Testing of Antimicrobial Peptides and Their Mimics
Published on: April 10, 2026
A practical, enantioselective synthetic route to a key precursor to the tetracycline antibiotics
Jason D Brubaker1, Andrew G Myers
1Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA.
Abstract:
A practical, enantioselective synthetic route to a key precursor to the tetracycline antibiotics is reported. The route proceeds in nine steps (21% yield) from the commercial substance methyl 3-hydroxy-5-isoxazolecarboxylate. Key steps in the route involve enantioselective addition of divinylzinc to 3-benzyloxy-5-isoxazolecarboxaldehyde and an endo-selective intramolecular furan Diels-Alder cycloaddition reaction. The route described has provided more than 40 g of chromatographically pure 1 with 93% ee.
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