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Total synthesis of Illudin C:
Reference: Aungst, R. A.; Chan, C.; Funk, R. L. Org. Lett. 2001, 3, 2611. DOI
Keywords: O-H → O-SO2R • Li/Br → Li-Vinyl • Ketone-1,3-di enolate+Alkyl-X • Alkyl-X+Enolate • Hydrogenolysis N-O • Alkyl-OH → Alkyl-I(2°) • Dehydrohalogenation → Ene • Dehydration → Enone • Li-Vinyl+Ketone • Nitrile oxide Cycloaddition • Oxime → Nitrile oxide •
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 •

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