PREPARATION OF 3-BENZOYLPENEMS AND PENEM AMIDES BY WITTIG METHODOLOGY

Authors
PEARSON ND SMALE TC SOUTHGATE R
Citation
Nd. Pearson et al., PREPARATION OF 3-BENZOYLPENEMS AND PENEM AMIDES BY WITTIG METHODOLOGY, Tetrahedron letters, 36(25), 1995, pp. 4493-4496
Citations number
6
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
25
Year of publication
1995
Pages
4493 - 4496
Database
ISI
SICI code
0040-4039(1995)36:25<4493:PO3APA>2.0.ZU;2-A
Abstract
Condensation of phenyl glyoxal with azetidin-2-ones (1a-c) gave the he mi-aminals (2a-c). Subsequent conversions produced the 4-(formylthio)p hosphoranes (4a-c) which gave on heating the 3-benzoylpenems (5a-c), f ormed by intramolecular Wittig cyclisation. Thermal isomerisation of t rans-6-substituted-3-benzoylpenems allowed the preparation of the cis- 6-substituted-3-benzoylpenems (7a-c). Using similar methodology the pe nem amides (7d-e) were synthesised.