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Stereoselective Solid‐Phase Synthesis of β ‐Lactams—A Novel Cyclization/Cleavage Step towards 1‐Oxacephams
Author(s) -
Furman Bartłomiej,
Thürmer René,
Kałuża Zbigniew,
Łysek Robert,
Voelter Wolfgang,
Chmielewski Marek
Publication year - 1999
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(19990419)38:8<1121::aid-anie1121>3.0.co;2-d
Subject(s) - solid phase synthesis , lactam , yield (engineering) , combinatorial chemistry , cleavage (geology) , derivative (finance) , stereochemistry , stereoselectivity , chemistry , organic chemistry , materials science , catalysis , peptide , biochemistry , fracture (geology) , economics , financial economics , metallurgy , composite material
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.