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

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