title: Stereoselective Solid-Phase Synthesis of β-Lactams-A Novel Cyclization/Cleavage Step towards 1-Oxacephams.
abstract: Despite the antibiotic activity and the attractiveness of β-lactams, the solid-phase synthesis of this class of compounds has been barely reported. Now the diastereoselective synthesis of the 1-oxacepham 2 from the resin-bound β-lactam derivative 1 has been achieved in five steps. The synthesis of 2 and other 1-oxacephams is attractive because all the reaction steps proceed in high yield, the purity of the product is high, and the reaction sequence is simple.
authors.affiliation: Institute of Organic Chemistry of the Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warszawa, Poland, Fax: (+48) 22-632-6681.
authors.forename: B
authors.initials: B
authors.lastname: Furman
authors.forename: R
authors.initials: R
authors.lastname: Thürmer
authors.forename: Z
authors.initials: Z
authors.lastname: Kałuża
authors.forename: R
authors.initials: R
authors.lastname: Lysek
authors.forename: W
authors.initials: W
authors.lastname: Voelter
authors.forename: M
authors.initials: M
authors.lastname: Chmielewski
keywords: Antibiotics; Cyclizations; Lactams; Solid-phase synthesis