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]