Preparation of 3-Benzoylpenems and Penem Amides by Wittig Methodology

DOI: 10.1016/0040-4039(95)00767-7

Source and publish data:

Tetrahedron Letters p. 4493 - 4496 (1995)

Update date:2022-07-30

Topics:

Authors:

Pearson, Neil D.

Smale, Terence C.

Southgate, Robert

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Article abstract of DOI:10.1016/0040-4039(95)00767-7

Condensation of phenyl glyoxal with azetidin-2-ones (1a-c) gave the hemi-aminals (2a-c).Subsequent conversions produced the 4-(formylthio)phosphoranes (4a-c) which gave on heating the 3-benzoylpenems (5a-c), formed by intramolecular Wittig cyclisation.Thermal isomerisation of trans-6-substituted-3-benzoylpenems allowed the preparation of the cis-6-substituted-3-benzoylpenems (7a-c).Using similar methodology the penem amides (7d-e) were synthesised.

Full text of DOI:10.1016/0040-4039(95)00767-7

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