2-(Alkylthio)penem-3-carboxylic acids. III. Synthesis of 6-ethylpenems.

Abstract
An N-protected derivative of 4-phenylthio-2-azetidinone (3b) was ethylated to give 3c, which was converted into the phosphorane 5d by the standard procedure. Intramolecular Wittig reaction of 5d afforded 6-ethylpenem esters 8a and 9a which were transformed via manipulation of the side chain to the amino acids 8d and 9d and subsequently to the acetamido derivatives 8e and 9e, which are 1-thia analogs of the antibiotic PS-5.

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