Total synthesis of β-Selinene:
| Reference: | Marshall, J. M.; Pike, M. T.; Carroll, R. D. J. Org. Chem. 1966, 31, 2933–2941. DOI |
| Reactions: | O-H → O-SO2Ar • Enone → Ketal • Hydroboration → Alkyl-OH • Jones oxidation • Alkyl-OH → Ketone • Ketone epimerization • Wittig-methyl • Ketal → Ketone • Ketone → Alkyl-OH • Alkyl-X → Alkyl-CN • Nitrile+Li-R → Ketone • Li-Me+Ketone • Ketone+Li-Alkyl • Wittig-methyl • |
| Reagents: | Glycol • TsOH • BH3·THF • H2O2, NaOH • CrO3, H2SO4 (Jones) • NaOMe • PPh3=CH2 • DMSO (solvent) • HCl, H2O • AlH4-Li+ • Cyanide, sodium • TsCl, Py • Me-Li • Chloride, ammonium • Me-Li • PPh3=CH2 • |