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Total synthesis of Vindoline New:
Reference: Kato, D,; Sasaki, y.; Boger, D. L. J. Am. Chem. Soc. 2010, 132, 3685-3687. DOI
Keywords: CarboxAcid → Alkyl-OH • O-H → O-MOM • CarboxAcid → CarboxAmide(Weinreb) • N-C(O)OR → N-H • N-H → N-C(O)NR2 • O-Bn → O-H • Alkyl-OH → Aldehyde • Ketone → Alkyl-OH • O-H → O-C(O)R • Carboxamide → Amine • O-MOM → O-H • Alkyl-OH → Aldehyde • Mechanism • N-H → N-C(O)OR • CarboxAmide(Weinreb)+Mg-R • Wittig-methoxymethyl • N-H → N-C(O)R • Mechanism • Oxadiazole formation • Diels-Alder-inverse, EnolEther • Retro-1,3-dipolar cycloaddition • Cycloaddition Carbonyl oxide • Aminal → Amine • N-H → N-Alkyl • Dehydration → Ene • Urea •
Reagents: BH4-Na+ • Cl-CH2-OR • H2, Pd • NMe(OMe)-H • Carbodiimide • DMAP • Alkyl-MgBr • CeCl3 • PPh3 • Fluoride, R4N+ • DMAP • NEtiPr2 • TsCl • NEt3 • BH3CN-Na+ • H2, Pd • Dess-Martin • AlH(OtBu)3-Li+ • Acetic anhydride • DMAP • MeOTf • BH4-Na+ • Pyridine, 2,6-di-tBu • DMSO, Py·SO3 (Parikh-Doering) • SiO2 • TsCl • DMAP • Acetate, sodium • BH(sBu3)-Li+ • PPh3, DEAD •

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