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Report | Regular issue | Vol 19, No. 9, 1982, pp.1647-1654
Published online, 1st January, 1970
DOI: 10.3987/R-1982-09-1647
Metal Catalyzed Decomposition Diazoketones and Diazoamides of β-Lactams Part I: Penicillin Route to Carbapenems?

Ching-Pong Mak, Karl Baumann, Friedrich Mayerl, Christa Mayerl, and Hans Fliri

*Sandoz Research Institute, A-1235 Vieena, Austria


Metal catalyzed decomposition of diazoketones and diazoamides derived from penicillanic acid were investigated as approaches towards the synthesis of the carbapenem nucleus. Diazoketones derived from C-3 gave products of insertion into the C-5/S bond with inversion of stereochemistry. Homologous diazoketones yielded the tricyclic aminodiketone 10, derived from carbene insertion into the amide bond exclusively. Attaching the diazo group to the amino function led either to insertion into solvent or gave decomposition products.