Total synthesis of Reserpine (Stork):
| Reference: | Stork, G. Pure Appl. Chem. 1989, 61 439 |
| Reactions: | O-Bn → O-H • Pictet-Spengler • Amine-6 • N-H → N-Alkyl • Amine-6 • Bicyclo(440)-aza • Si-Alkyl → HO-Alkyl • ConjAdd Enolate • Bicyclo(222) • Bicyclo(322)-oxa • Lactone-7 • O-H → O-Me • Lactone → Lactol • CompRed-Lactone/CarboxEster+M-H • Aldehyde → Cyanoamine • Cyanide+Aldehyde • O-H → O-SO2Ar • Baeyer-Villiger • Si-Aryl → Si-F • |
| Reagents: | Fluoride, R4N+ • H2, Pd • TsCl • MeI • Ag2O • AlHiBu2 • Cyanide, potassium • HCl, THF • Vinyl-SiR3 • Acrylate • Perbenzoic acid, 3-chloro • |