Total synthesis of Epoxyeujindole A:
| Reference: | Lu, Z.; Li, H.; Bian, M.; Li, A. J. Am. Chem. Soc. 2015, 137, 13764-13767. DOI |
| Reactions: | Al-R → Cu-R • Mg-R → Ce-R • ConjAdd-Alkylation • Ketone enolate+Alkyl-X • Cu-Me+Enone • Allyl-X+Enolate • Epoxidation, peracid • Pinacol • Aldol-Na → Enone • Cyclohexenone • Bicyclo(440) • Ketone → EnolEther • Ketone → Ketone-γ-OR • Iodoetherification • ConjAdd Cu-R (intram) • Cu-Alkyl+Enone • Zn-R → Cu-R • Ketone → EnolTriflate • Pd/Sn-Alkyl+Vinyl-X • Alkyl-OH → Alkyl-I • Nozaki-Hiyama coupling • Cr-Allyl+Aldehyde • Aldehyde+Cr-R • Hydrogenation Alkene • Alkyl-OH → Ketone • Ketone → EnolTriflate • Pd/B-Aryl+Vinyl-X • Indole synthesis • Ketone+Mg-Alkyl • Alkyl-OH → Ketone • Ketone+Ce-R • Ce-Alkyl+Ketone • Lactol → Lactone • Lactone-5 • Electrocyclic-6π • Cationic cyclization • Friedel-Crafts Vinylation, Ene • Cyclohexene • Cationic cyclization • Cyclohexene • Ether-5 • Bicyclo(321)-oxa • Friedel-Crafts Alkylation, Ene • N-SO2R → N-H • |
| Reagents: | Me-Li • AlMe3 • HMPA (solvent) • Allyl-I • Vinyl-SiR3 • Acetic acid, trifluoro • NaOMe • TsOH • Orthoformate • Oxone • Vinyl-OR • NIS • CuI • LiN(SiMe3)2 • Tf2NPh • SnBu3-CH2-OR • Pd(PPh3)4 • PPh3, I2 • CrCl2 • Acetaldehyde • H2, RaNi • RuO4-Pr4N+, NMO • KN(SiMe3)2 • Tf2NPh • Pd(PPh3)4 • Me-MgBr • RuO4-Pr4N+, NMO • Me-MgBr • CeCl3 • HClO4 • RuO4-Pr4N+, NMO • BF3·OEt2 • AlHiBu2 • TsOH • Perbenzoic acid, 3-chloro • |