Enantioselective total syntheses of trichodermamides A and B.
Starting from commercially available (-)-quinic acid, the enantioselective total syntheses of trichodermamides A and B were achieved. The key reactions involve the stereoselective construction of the oxazine ring via an intramolecular epoxide ring opening reaction and an EDCI-assisted peptide coupling reaction.
Wan
Xiaobo
X
Chemistry Department, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA.
Joullié
Madeleine M
MM
D045744:Cell Line, Tumor; D002621:Chemistry / Q000379:methods; D002626:Chemistry, Pharmaceutical / Q000379:methods; D018360:Crystallography, X-Ray; D004151:Dipeptides / Q000138:chemical synthesis*; D015195:Drug Design; D004852:Epoxy Compounds / Q000737:chemistry; D005658:Fungi / Q000378:metabolism; D006801:Humans; D020128:Inhibitory Concentration 50; D008956:Models, Chemical; D010078:Oxazines / Q000737:chemistry; D010100:Oxygen / Q000737:chemistry; D010455:Peptides / Q000737:chemistry
D004151:Dipeptides; D004852:Epoxy Compounds; D010078:Oxazines; D010455:Peptides; C476747:trichodermamide A; C476748:trichodermamide B; D010100:Oxygen