image

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 • 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) • N-H → N-Alkyl • N-H → N-Alkyl • Lactone-9+ • Si-Vinyl → H-Vinyl • CarboxAcid → CarboxAmide • Li/H → Li-Vinyl-OR • Li-Vinyl → Zn-Vinyl •
Reagents: Chiral auxiliary-Menthol • Alkynyl-Li • BH4-Na+, CeCl3 • NaH • BnOC(=NH)CCl3 • H2, Pt • Acetic acid, trifluoro • LiN(SiMe3)2 • SePh-Cl • Ketene acetal • BF3·OEt2 • BH4-Na+, CeCl3 • S=C(Imid)2 • DMAP • HSnBu3 • Hydroxide, potassium • Oxalyl chloride • Hydroxide, potassium • Sulfonyl chloride, methane, NEt3 • Carbonate, potassium • Na°/NH3 • Sulfonyl chloride, methane • NMe(OMe)-AlMe2 • TfOH • LiNiPr2 • ZnCl2

Syntheses Home