An enantioselective synthesis of differentially protected erythro-alpha,beta-diamino acids and its application to the synthesis of an analogue of rhodopeptin B5.
Methodology for the enantioselective synthesis of differentially protected erythro-alpha,beta-diamino acids from N-tosyloxy beta-lactams is reported. The requisite N-tosyloxy beta-lactams are readily available from simple beta-keto esters. The reported approach is flexible and compatible with a variety of functional groups. The synthetic utility of the method is demonstrated through its application to the preparation of an analogue of the antifungal cyclic peptide rhodopeptin B5.
Durham
Timothy B
TB
Department of Chemistry and Biochemistry, 251 Nieuwland Science Hall, University of Notre Dame, Notre Dame, Indiana 46556-5670, USA.
Miller
Marvin J
MJ
D000596:Amino Acids / Q000138:chemical synthesis*; D000935:Antifungal Agents / Q000138:chemical synthesis*; D020650:Combinatorial Chemistry Techniques; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010456:Peptides, Cyclic / Q000138:chemical synthesis*; D013237:Stereoisomerism; D047090:beta-Lactams / Q000138:chemical synthesis*
D000596:Amino Acids; D000935:Antifungal Agents; D010456:Peptides, Cyclic; D047090:beta-Lactams; C401441:rhodopeptin B5