Total synthesis of DOPA, L- (Monsanto):
| Reference: | Knowles, W. S. Acc. Chem. Res. 1983, 16, 106-112. DOI, Nobel Lecture |
| Reactions: | Arbuzov • N-C(O)R → N-H • Oxidative coupling Li-Phosphine • Mg-Aryl+Phosphinate • Phosphinate+Mg-R • Phosphine oxide → Phosphine • Azlactone • Hydrogenation EnoateEster (asym) • EnoateEster Hydrogenation (asym) • Mg-Aryl+Phosphite • Phosphinate • |
| Reagents: | P(OMe)3 • Aryl-MgX • SOCl2 • Aryl-MgX • LiNiPr2 • CuCl2 • NBu3 • Acetic anhydride • Menthol • Pyridine • DIPAMP • MeI • |