Total synthesis of Triquinacene:
| Reference: | Woodward, R. B.; Fukanage, T.; Kelly, R. C. J. Am. Chem. Soc. 1964, 86, 3162-3164. DOI |
| Reactions: | CarboxAnhydride → CarboxAcid • CarboxEster → CarboxAcid • CarboxAcid → CarboxCl • Cope elimination • Alkyl-OH → Ketone • Epoxidation, peracid • Curtius • C-CO2H → C-N • CarboxCl → CarboxAzide • CarboxAcid → CarboxCl • Alkyl-OH → Ketone • N-C(O)OR → N-CH3 • Reductive amination, HCO2H • Leuckart • Eschweiler-Clarke methylation • Ketone enolate+Epoxide • Epoxide+Enolate • Cyclopentane • CarboxEster epimerization • Amine → AmineOxide • CarboxAcid → CarboxEster • |
| Reagents: | CrO3·Py2 (Collins) • Peracetic acid • CrO3, H2SO4 (Jones) • Pb(OAc)4 • Diazomethane • HOMe (react) • NaOMe • Hydroxide, sodium • SOCl2 • Azide, sodium • AlH4-Li+ • Formaldehyde • Formic acid • H2O2 • KOtBu • |