Progress towards the total synthesis of trichodermamides A and B: construction of the oxazine ring moiety.
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]
Wan
Xiaobo
X
Chemistry Department, University of Pennsylvania, 231 South 34th Street, Philadelphia, PA 19104, USA.
Doridot
Gabriel
G
Joullié
Madeleine M
MM
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
D004151:Dipeptides; D004852:Epoxy Compounds; D010078:Oxazines; C476747:trichodermamide A; C476748:trichodermamide B; D011801:Quinic Acid