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Total synthesis of Adaline:
Reference: Itoh, T.; Yamazaki, N.; Kibayashi, C. Org. Lett. 2002, 4, 2469. DOI
Keywords: Alkyl-OH -> Aldehyde --- N-H -> N-C(O)H --- Alkene -> Diol-1,2 --- O-H -> O-SiMe2tBu --- O-H -> O-C(S)SR --- O-SiMe2tBu -> O-H --- N-CHO -> N-H --- Alkyl-OH -> Ketone --- Barton-McCombie reduction --- Alkyl-OH -> Alkyl-H --- RCM -> Ring-N --- Amine-6 --- Si-Allyl+Iminium --- Li-Alkynyl+Iminium --- Amine-6 --- Hydrogenation-Lindlar --- Amine -> Formamide --- CarboxAmide -> Alkyl-OH --- CarboxAcid -> CarboxAmide --- Lactam-6
Reagents: TiCl4 --- Allyl-Si --- BH3NH2-Li+ --- RuO4-Pr4N+, NMO --- Alkynyl-Li --- Orthoformate --- TsOH --- H2, Pd --- OsO4, NMO --- NEt3 --- CS2 --- HSnBu3 --- Fluoride, Bu4N+ --- Li°/H2NCH2CH2NH2 --- CrO3Cl·PyH (PCC) --- Grubbs II --- AIBN

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