Total synthesis of Vincorine:
| Reference: | Horning, B. D.; MacMillan, D. W. C. J. Am. Chem. Soc. 2013, 135, 6442-6445. DOI |
| Reactions: | N-H → N-Me • Li/H → Li-Indole • Li-R → Zn-R • Iminium catalysis • Diels-Alder, Enal (asym) • Bicyclo(430)-aza • Pinnick oxidation • Aldehyde → CarboxAcid • Iminium+N-R • EnAmine → Aminal • Radical cyclization(Alkyl) • Allene synthesis • Allene Hydrogenation • CarboxAcid → CarboxEster(telluro) • Reductive amination, B-H • Pd/Zn-Aryl+Vinyl-X • Indole synthesis • Amine-5 • Propellane(433)-aza • Amine-7 • Bicyclo(322)-aza • |
| Reagents: | Propiolaldehyde • Ditelluride, phenyl • NaH • MeI • BuLi(n) • ZnCl2 • Vinyl-I • HBF4 • Chlorite, sodium • NMO • BH4-Na+ • BH(OAc)3-Na+ • Acetic acid, trifluoro • H2, Pd • O=C(OR)Cl • PdCl2 • |