Total synthesis of Scopadulcic Acid B:
| Reference: | Overman, L. E.; Ricca, D. J.; Tran, V. D. J. Am. Chem. Soc., 1993, 115, 2042. DOI |
| Reactions: | O-H → O-SiMe2tBu • Carbene Cycloaddition • Cyclopropane • Li/Br → Li-Cyclopropyl • Mg-Cyclopropyl+Aldehyde • Aldehyde+Mg-R • CompE+-Aldehyde/Aryl-I+M-R • Li-R → Mg-R • Mg-Allyl+Aldehyde • Aldehyde+Mg-R • Hydroboration → Alkyl-OH • Alkyl-OH → Ketone • Ketone → EnolSilane • Radical reduction(C-Br) • Alkyl-X → Alkyl-H(2°) • Alkyl-OH → Aldehyde • O-H → O-SiMe2tBu • CompNu-O-H/O-H+R3Si-X • O-H → O-C(O)R • O-SiMe2tBu → O-H • Wolff-Kishner • Aldehyde → CH3 • Nitrile → Imine • Alkyl-OR → Ketone • Alkyl-OH → CarboxAcid • Enone → Allyl-OH • Birch alkylation • CarboxAcid enolate+Alkyl-X • Alkyl-X+Enolate • Bicyclo(440) • ConjAdd M-CN • Hydrogenation alkene • CarboxEster → Alkyl-OH • Allyl-OH → Enone • CompOx-Allyl-OH/Alkyl-OH+MnO2 • Epoxidation, peracid • CompOx-Alkene/Enone+Peracid • Epoxide reduction • ConjReduct Enone • Li/H → Li-Aryl • Pd-Heck coupling • Cyclohexenone • Bicyclo(321) • Bicyclo(440) • Enone → Dienone • Li-Aryl+CO2 • O-H → O-Me • Ketone → Alkyl-OH • Cope rearrangement • Cycloheptane • O-SiMe2tBu → O-H • Wittig-methyl • Alkyl-OH → Ketone • |
| Reagents: | SiMe3-OTf • BuLi(tert) • Cr2O7·2PyH (PDC) • Allyl-MgX • Imidazole • BH3·SMe2 • H2O2, NaOH • DMSO, (COCl)2 (Swern) • HSnBu3 • CHBr3 • MgBr2 • AlH4-Li+ • Hydrazine • SiMe2tBu-OTf • Lutidine • Benzoyl triflate • Lutidine • Fluoride, R4N+ • RuCl3 • Periodate, sodium • Li°/NH3 • MeI • Al2O3 • AlH4-Li+ • MnO2 • Cyanide, AlR2 • DDQ • Perbenzoic acid, 3-chloro • BH4-Na+ • AlH4-Li+ • MeOTf • Pyridine, 2,6-di-tBu • AlH4-Li+ • BuLi(n) • CO2 • Aryl-Li • TsOH·Py • PPh3=CH2 • Fluoride, R4N+ • CrO3Cl·PyH (PCC) • Pd(OAc)2 • |