Total synthesis of Hapalindole Q New:
| Reference: | Vaillancourt, V.; Albizati, K. F. J. Am. Chem. Soc. 1993, 115, 3499-3502. DOI |
| Reactions: | PdCl2(PPh3) • N-H → N-SiiPr3 • Aryl-H → Aryl-Br • Ketone → EnolCarboxylate • Pd-enolate arylation • Grob fragmentation • Aldol-Na → Aldol • Ketone enolate+Aldehyde • O-H → O-SO2Me • Dehydrosulfonoxylation → Ene • Reductive amination, B-H • |
| Reagents: | NaH • DMF (solvent) • SiiPr3-Cl • Tribromide • LiNiPr2 • Acetic anhydride • PdCl2 • Na°/Naphth • Acetaldehyde • Sulfonyl chloride, methane, NEt3 • DMAP • Iodide, sodium • HMPA (solvent) • BH3CN-Na+ • Acetate, ammonium • S=C(Imid)2 • |