Enantioselective Synthesis of Monocyclic β-Lactams Related to Nocardicins via a [2 + 2] Cycloaddition Reaction

OSAMU NAKAGUCHI; TERUO OKU; HIDEKAZU TAKENO; MASASHI HASHIMOTO; TAKASHI KAMIYA

doi:10.1248/cpb.35.3985

Enantioselective Synthesis of Monocyclic β-Lactams Related to Nocardicins via a [2 + 2] Cycloaddition Reaction

OSAMU NAKAGUCHI, TERUO OKU, HIDEKAZU TAKENO, MASASHI HASHIMOTO, TAKASHI KAMIYA

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Keywords: stereochemistry, ketene-imine cycloaddition, 3-aminonocardicinic acid, nocardicin, antibacterial activity, structure-activity relationship

JOURNAL FREE ACCESS

1987 Volume 35 Issue 10 Pages 3985-3994

DOI https://doi.org/10.1248/cpb.35.3985

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Abstract

Monocyclic β-lactams related to nocardicins were enantioselectively synthesized from phthal-imidoacetyl chloride and hexahydro-1, 3, 5-triazines (4) via a [2+2] cycloaddition reaction. The preparation and biological activity of some typical acyl derivatives are also described.

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