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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
Keywords: 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+Li-R • N-H → N-Alkyl • Amine-6 • Bicyclo(222) • 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-SO2R • Benzyl-H → Benzyl-OH • Allylic oxidation → Allyl-OH • Li-Benzyl+O2
Reagents: AlMe3 • SiMe2tBu-Cl • LiNiPr2 • Iodoethanol • TsOH·Py • AlHiBu2 • PPh3=CH-OMe • PPh3, DEAD • HCl, H2O • Benzyl-Li • BH4-Na+ • HF • Sulfonyl chloride, methane, Py • NaH • O2 • Azide, diphenylphosphoryl • AlMe2-NR2 • Imidazole • DMSO (solvent) • DMSO, (COCl)2 (Swern) • PPh3

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