Synthesis of racemic, 2-(alkylthio)-6-(1-hydroxyethyl) penems; attempted penem synthesis via copper (I)-promoted cyclisations

…, AK Ganguly, VM Girijavallabhan, PD Jeffrey, S Lin…

文献索引：McCombie, S. W.; Ganguly, A. K.; Girijavallabhan, V. M.; Jeffrey, P. D.; Lin, S.; at al. Tetrahedron Letters, 1981 , vol. 22, # 36 p. 3489 - 3492

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被引用次数: 16

摘要

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-azabicyc1o [3.2. 0]-hept-3-enes) as the sole bicyclic product.