Total synthesis of Illudin C:
| Reference: | Aungst, R. A.; Chan, C.; Funk, R. L. Org. Lett. 2001, 3, 2611. DOI |
| Reactions: | O-H → O-SO2Me • Li/Br → Li-Vinyl • Ketone-1,3-di enolate+Alkyl-X • Alkyl-X+Enolate (intram) • N-OR → N-H • Imine → Ketone • Alkyl-OH → Alkyl-I (2°) • Dehydration → Enone • Li-Vinyl+Ketone • Nitrile oxide Cycloaddition • Cyclohexene • Bicyclo(430) • Spiro(52) • Oxime → Nitrile oxide • Cyclopropane • Ketone → Alkyl-OH • Aldehyde → Oxime • Dehydrohalogenation → Ene • |
| Reagents: | POBr3 • DMF (react) • NH2OH • Vinyl-Li • Ethylene dibromide • AlH(OtBu)3-Li+ • PPh3, I2 • DBU • BuLi(tert) • H2, RaNi • Sulfonyl chloride, methane, NEt3 • DBU • Vilsmeier reagent • Imidazole • TsNClNa • |