Total synthesis of Shikimic Acid (Smissman):
| Reference: | Smissman, E. E.; Suh, J. T.; Oxman, N.; Daniels, R J. Am. Chem. Soc. 1962, 84, 1040-1041. DOI |
| Reactions: | Diels-Alder, EnoateEster • Ester Pyrolysis • Alkene → Diol-1,2 • Ketal → Diol-1,2 • CarboxEster → CarboxAcid • |
| Reagents: | OsO4 • Butadiene, 1-OR • Acrylate • Acetone (react) • Chloride, calcium • Acetic acid • Hydroxide, sodium • |