Total synthesis of Ilimaquinone:
| Reference: | Bruner, S. D.; Radeke, H. S.; Tallarico, J. A.; Snapper, M. L. J. Org. Chem. 1995, 60, 1114-1115. DOI |
| Reactions: | Robinson annulation, diketone • Cyclohexenone • Bicyclo(440) • Ketone → Alkyl-OH • CompRed-Ketone/Enone+M-H • ConjReduct-Alkylation • ConjReduct Enone • Ketone enolate+Alkyl-X • Wittig-methyl • Hydrogenation Alkene • Alkyl-OH → Ketone • Wittig-methyl • Quinone synthesis • Aryl-Cl → Aryl-OH • Pd-Aryl-X → Aryl-OH • |
| Reagents: | BH4-Na+ • Li°/NH3 • Benzyl-X • PPh3=CH2 • DMSO (solvent) • H2, Pt • CrO3Cl·PyH (PCC) • PPh3=CH2 • DMSO (solvent) • Pd(PPh3)4 • Bicarbonate, sodium • Ceric ammonium nitrate • |