Total synthesis of Quinine (Stork):
| Reference: | Stork, G.; Niu, D.; Fujimoto. A.; Koft, E. R.; Balkovec, J. M.; Tata, J. R.; Dake, G. R. J. Am. Chem. Soc. 2001, 123, 3239. DOI |
| Reactions: | Wittig-methoxymethyl • Reductive formylation • Mitsunobu → Azide • Alkyl-OH → Alkyl-N3 • CarboxAmide enolate+Alkyl-X • Alkyl-X+Enolate • Li-Benzyl+Aldehyde • Aldehyde+Li-R • CompE+-Aldehyde/Azide+M-R • Quinoline synthesis • N-H → N-Alkyl • Amine-6 • Bicyclo(222)-aza • Staudinger • Azide → Amine • Ketone → Imine • Amine-6 • Lactone → CarboxAmide • O-H → O-SiMe2tBu • O-SiMe2tBu → O-H • Lactone-5 • Lactone → Lactol • Enol → Aldehyde • Alkyl-OH → Ketone • Imine → Amine • O-SiPh2tBu → O-H • O-H → O-SO2Me • Benzylic oxidation → Benzyl-OH • Li-Benzyl+O2 • |
| Reagents: | AlMe2-NR2 • SiMe2tBu-Cl • LiNiPr2 • Iodoethanol • TsOH·Py • AlHiBu2 • PPh3=CH-OR • PPh3, DEAD • HCl, H2O • Benzyl-Li • BH4-Na+ • HF • Sulfonyl chloride, methane, Py • NaH • O2 • Azide, diphenylphosphoryl • Imidazole • DMSO (solvent) • DMSO, (COCl)2 (Swern) • PPh3 • AlMe3 • NHEt2 • |