Gamma-Lactams and the Reformatsky Reaction: New Tricks for an Old Reaction

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A large fraction of the world's antibiotic arsenal depends on the 4-membered beta-lactam ring as the active functional group. An alternative to the beta-lactam is the 5-membered gamma-lactam structure, which has formed the core of several compounds that have been reported to possess antibiotic activity. The use of Reformatsky-type chemistry to form beta-lactams has been known since the 1940's, but to date Reformatsky-type chemistry has not been reported for the preparation of gamma-lactams. In principle, the reaction between ketones or aldehydes based on alpha-amino acids and Reformatsky reagents should cyclize and afford gamma-lactams directly. In this talk we wish to report on our success to date.<\/p>" ] } }, { "label": { "en": [ "navDate" ] }, "value": { "en": [ "May 7th at 12:11pm" ] } }, { "label": { "en": [ "license" ] }, "value": { "en": [ "http:\/\/rightsstatements.org\/vocab\/InC-EDU\/1.0\/" ] } } ], "within": "https://arches.union.edu/steinmetzsymposium", "partOf": [ { "id": "https://arches.union.edu/steinmetzsymposium/metadata/iiifmanifest3collection/default.jsonld", "type": "Manifest" } ], "items": [{ "id": "https://arches.union.edu/do/daa62c01-ba96-4a08-a1d2-be363531bae0/iiif/canvas/p1", "type": "Canvas", "label": { "en": [ "Video:Gamma-Lactams and the Reformatsky Reaction: New Tricks for an Old Reaction"]}, "width": 1686, "height": 768, "duration": 969545, "items": [ { "id": "https://arches.union.edu/do/daa62c01-ba96-4a08-a1d2-be363531bae0/iiif/page/p1", "type": "AnnotationPage", "items": [ { "id": "https://arches.union.edu/do/daa62c01-ba96-4a08-a1d2-be363531bae0/iiif/annotation/p1", "type": "Annotation", "motivation": "painting", "body": { "id": "https://arches.union.edu/do/54829/iiif/b3b79014-354c-4cc8-88b4-8d2e716093ef/full/full/0/Gamma_Lactam_Reformatsky.mp4", "type": "Video", "format": "video/mp4", "duration": 969545, "height": 768, "width": 1686 }, "target": "https://arches.union.edu/do/daa62c01-ba96-4a08-a1d2-be363531bae0/iiif/canvas/p1" } ] } ] } ], "structures": [ { "id": "https://arches.union.edu/do/daa62c01-ba96-4a08-a1d2-be363531bae0/iiif/range/r1", "type": "Range", "label": { "en": [ "Gamma-Lactams and the Reformatsky Reaction: New Tricks for an Old Reaction" ] }, "items": [ { "id": "https://arches.union.edu/do/daa62c01-ba96-4a08-a1d2-be363531bae0/iiif/canvas/p1", "type": "Canvas" } ] } ] }