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Total synthesis of Cannabisativine:
Reference: Kuethe, J. T.; Comins, D. L. J. Org. Chem., 2004, 69, 5219-5231 DOI
Keywords: Luche reduction --- Ynone -> Propargyl-OH --- O-H -> O-Bn --- Enone -> Enone-α-Seleno --- Luche reduction --- Ketone -> Alkyl-OH --- CarboxEster -> CarboxAcid --- CarboxAcid -> CarboxCl --- N-CO2R -> N-H --- N-SO2R -> N-H --- O-Bn -> O-H --- CarboxAmide(Weinreb)+Li-Alkynyl --- Ketene acetal+Enone-β-Amino --- ConjAdd Ketene acetal --- Reductive elimination - PhSe/OR --- Zn-Vinyl-OR+Pyridinium --- Hydrogenation-Alkyne --- CarboxEster -> CarboxAmide(Weinreb) --- Amine+Alkyl-X --- N-H -> N-Alkyl --- Lactone-14 --- H/Si -> Enone --- CarboxAcid -> CarboxAmide --- Li/H -> Li-Vinyl-OR --- Li-Vinyl -> Zn-Vinyl
Reagents: Alkynyl-Li --- BH4-Na+, CeCl3 --- NaH --- BnOC(=NH)CCl3 --- H2, Pt --- CF3CO2H --- LiN(SiMe3)2 --- PhSeCl --- CH2=C(OR)(OSiR'3) --- BF3 --- BH4-Na+, CeCl3 --- S=C(Im)2 --- DMAP --- HSnBu3 --- Hydroxide, potassium --- Oxalyl chloride --- Hydroxide, potassium --- MeSO2Cl, NEt3 --- Carbonate, potassium --- Na*/NH3 --- MeSO2Cl --- NMe(OMe)-AlMe2 --- TfOH --- LiNiPr2 --- ZnCl2

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