Total synthesis of Quebrachamine New:
| Reference: | Kutney, J. P.; Abdurahman, N.; Gietsos, C.; Le Quesne, P.; Piers, E.; Vlattas, I. J. Am. Chem. Soc. 1970, 92, 1727-1735. DOI |
| Reactions: | O-H → O-Bn • Alkyl-OH → Alkyl-Cl • Malonic Ester Synthesis • CarboxEster enolate+Alkyl-X • Alkyl-X+Enolate • CarboxEster → CarboxAcid • Decarboxylation malonic • CarboxAcid → CarboxEster • CarboxEster enolate+Alkyl-X • Bromoacetate+Enolate • Amine → Imide • Lactam-5 • N-C(O)R → N-CH2R • Amine-5 • Amine → Imine • Friedel-Crafts Alkylation • Amine-6 • Bicyclo(430)-aza • O-Bn → O-H • O-H → O-SO2Me • Amine → Ammonium • Amine-6 • Ammonium → Amine • |
| Reagents: | SOCl2 • Malonate • NaOEt • Hydroxide, potassium • HOEt (react)} • NaH • DMSO (solvent) • NaCH2S(O)CH3 • Bromoacetate • AlH4-Li+ • H2, Pd • Acetic acid • Sulfonyl chloride, methane, NEt3 • Hg(OAc)2 • AlH4-Li+ • Piperidine • H2SO4 • |