Total synthesis of Sativene (McMurry):
| Reference: | McMurry, J. E. J. Am. Chem. Soc., 1968, 90, 6821. DOI |
| Reactions: | Ketone → Hydrazone • Hydrogenation Enone • Ketone+Mg-Alkyl • Mg-Alkyl+Ketone • Protecting group - Ketone • CompRed-Alkene/Imine+M-H • Dehydration → Ene • Ketone → C=CH2 • Ketone enolate+Alkyl-X (intram) • Alkyl-X+Enolate (intram) • Bicyclo(221) • Cyclopentanone • Ketone+Li-Alkyl • Li-Me+Ketone • Ozonolysis C=N • Ketone → Ketal • CompE+-Ketone/Ketone+glycol • O-H → O-SO2Ar • Hydroboration → Alkyl-OH • Dehydration → Ene • |
| Reagents: | Glycol • H2, Pd • Alkyl-MgX • H2SO4 • Hydrazine, phenyl • H2O2, KOH • O3 • TsCl, Py • NaCH2S(O)CH3 • DMSO (solvent) • Me-Li • SOCl2 • Wieland-Miescher • |