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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-SeR • Luche reduction • Ketone -> Alkyl-OH • CarboxEster -> CarboxAcid • CarboxAcid -> CarboxCl • N-C(O)OR -> N-H • N-SO2R -> N-H • O-Bn -> O-H • CarboxAmide(Weinreb)+Li-R • Li-Alkynyl+CarboxAmide(Weinreb) • Li/H -> Li-Alkynyl • Ketene acetal+Enone • Enone-β-Amino+Enolsilane • ConjAdd Ketene acetal • Reductive elimination - Se/OR • Zn-Vinyl-OR+Pyridinium • Pyridinium+M-R • Hydrogenation Alkyne • CarboxEster -> CarboxAmide(Weinreb) • Amine+Alkyl-X • N-H -> N-Alkyl • Lactone-14 • Si-Vinyl -> H-Vinyl • CarboxAcid -> CarboxAmide • Li/H -> Li-Vinyl-OR • Li-Vinyl -> Zn-Vinyl • Chiral auxiliary •
Reagents: Alkynyl-Li • BH4-Na+, CeCl3 • NaH • BnOC(=NH)CCl3 • H2, Pt • Acetic acid, trifluoro • LiN(SiMe3)2 • SePh-Cl • CH2=C(OR)(OSiR'3) • BF3·OEt2 • 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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