Total synthesis of Fawcettimine:
| Reference: | Heathcock, C. H.; Blumenkopf, T. A.; Smith, K. M. J. Org. Chem. 1989, 54, 1548-1562. DOI |
| Reactions: | Arndt-Eistert • Diazoketone → Ketene • Sakurai allylation • Si-Allyl+Enone • Enone+Si-R • ConjAdd Si-Allyl • Allyl-OH → Enal • CarboxEster → CarboxAcid • CompE+-CarboxEster/Nitrile+H2O • CarboxCl → Diazoketone • CarboxAcid → CarboxCl • CarboxEster → Alkyl-OH • Nitrile → Amine • Ketone → Alkyl-OH • Wittig-carboxymethyl → EnoateEster • Ketone enolate+EnoateEster • ConjAdd Enolate • Cyclopentane • Bicyclo(430) • O-H → O-SO2Ar • N-H → N-SO2R • N-H → N-Alkyl • Amine-9+ • N-SO2R → N-H • Alkyl-OH → Ketone • Ozonolysis • |
| Reagents: | Allyl-SiR3 • TiCl4 • CrO3·Py2 (Collins) • Hydroxide, sodium • Oxalyl chloride • Diazomethane • NEt3 • HOMe (react) • AlH4-Li+ • DMAP • CrO3 • O3; Me2S • Na°/Naphth • HClO4 • Bicarbonate, sodium • Formate, ethyl • NaOEt • DMF (solvent) • |