Synthesis of racemic, 2-(alkylthio)-6-(1-hydroxyethyl) penems; attempted penem synthesis copper (I) - promoted cyclisations |
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| Authors: | SW McCombie AK Ganguly VM Girijavallabhan PD Jeffrey S Lin P Pinto AT McPhail |
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| Institution: | Chemical Research, Schering Corporation, Bloomfield, N.J. 07003 USA;Department of Chemistry, Duke University, Durham, N.C. 27706 USA |
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| Abstract: | Stereocontrolled syntheses of the diastereoisomeric 6-(1-hydroxyethyl)-2-ethylthio and 2-(2-aminoethylthio)-penem-3-carboxylates from a common monocyclic azetidinone precursor are described. Cu (I)-promoted cyclisation of suitable N/C-3 secopenems is shown to yield “isopenems” (7-oxo-2-thia-1-azabicyc1o3.2.0]-hept-3-enes) as the sole bicyclic product. |
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