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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-SiR3 • 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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