Total synthesis of Physostigmine (partial):
| Reference: | Espejo, V. R.; Li, X.-B.; Rainier, J. D. J. Am. Chem. Soc. 2010, 132, 8283. DOI |
| Reactions: | CompE+-CarboxAmide/Carbamate+KOH • N-Boc → N-H • Cyclopropane • Bicyclo(210)-aza • Bromoamination Alkene • Amine-5 • Bicyclo(330)-aza • CarboxAcid → CarboxEster • Reductive amination, H2 • Eschweiler-Clarke methylation • Cyclopropane alkylation • Barton decarboxylation • CarboxEster enolate+Alkyl-X (3°) • Alkyl-X+Enolate (intram) • |
| Reagents: | TsOH·Py • KOtBu • Hydroxide, sodium • Mercaptopyridine-N-oxide • Thiol, t-butyl • SiMe3-I • Formaldehyde • H2, Pd • AlMe3 • NBS • Carbodiimide • |