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

Journal Article (Journal Article)

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. © 1981.

Full Text

Duke Authors

Cited Authors

  • McCombie, SW; Ganguly, AK; Girijavallabhan, VM; Jeffrey, PD; Lin, S; Pinto, P; McPhail, AT

Published Date

  • January 1, 1981

Published In

Volume / Issue

  • 22 / 36

Start / End Page

  • 3489 - 3492

International Standard Serial Number (ISSN)

  • 0040-4039

Digital Object Identifier (DOI)

  • 10.1016/S0040-4039(01)81939-0

Citation Source

  • Scopus