2-(Alkylthio)penem-3-carboxylic acids I. Synthesis of 6-unsubstituted penems.

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Treatment of 4-acetoxy-2-azetidinone (9) with various sodium alkyl trithiocarbonates gave 4-[(alkylthio) thiocarbonyl] thioazetidinones 10, which were converted into the phosphoranes 8. Intramolecular Wittig reactions of 8 followed by deblocking yielded penem-3-carboxylic acids 5.

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