title: Progress towards the total synthesis of trichodermamides A and B: construction of the oxazine ring moiety.
abstract: Trichodermamides are modified heterocyclic dipeptides that possess a unique 4H-5,6-dihydro-1,2-oxazine ring. Starting from affordable, easily available (-)-quinic acid, the enantioselective synthesis of this oxazine moiety was achieved by an intramolecular epoxide ring-opening reaction by an oxime. [structure: see text]
authors.affiliation: Chemistry Department, University of Pennsylvania, 231 South 34th Street, Philadelphia, PA 19104, USA.
authors.forename: Xiaobo
authors.initials: X
authors.lastname: Wan
authors.forename: Gabriel
authors.initials: G
authors.lastname: Doridot
authors.forename: Madeleine M
authors.initials: MM
authors.lastname: Joullié
mesh_terms: D002384:Catalysis; D004151:Dipeptides / Q000138:chemical synthesis*; D004852:Epoxy Compounds / Q000737:chemistry; D008956:Models, Chemical; D010078:Oxazines / Q000737:chemistry*; D011801:Quinic Acid / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D004151:Dipeptides; D004852:Epoxy Compounds; D010078:Oxazines; C476747:trichodermamide A; C476748:trichodermamide B; D011801:Quinic Acid