Total synthesis of Cocaine (Tufariello):
| Reference: | Tufariello, J. J.; Mullen, G. B. J. Am. Chem. Soc. 1978, 100, 3638. DOI |
| Reactions: | Nitrone synthesis • Nitrone Cycloaddition • Nitrone Cycloaddition • Nitrone Retro-Cycloaddition • Retro-1,3-dipolar cycloaddition • Nitrone Cycloaddition • Amine-6 • Bicyclo(321)-aza • N-OR → N-H • O-H → O-C(O)R • Amine → Ammonium • Dehydration → Enoate • |
| Reagents: | Acrylate • Sulfonyl chloride, methane, Py • DBN • MeI • Zn° • Benzoyl chloride • Perbenzoic acid, 3-chloro • |