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Total synthesis of Bilobalide:
Reference: Corey, E. J.; Su, W. J. Am. Chem. Soc. 1987, 109, 7534
Keywords: Enone -> Allyl-OH --- Aldehyde -> Acetal(Me) --- CarboxEster -> Alkyl-OH --- Alkyl-OH -> Aldehyde --- Aldehyde -> Acetal(Me) --- Aldehyde -> CarboxAcid --- Lactone-5 --- Epoxide -> Diol --- O-H -> O-C(O)R --- Aldehyde -> CarboxAcid --- Alkene -> Diol-1,2 --- CarboxEster enolate+Ynone --- Epoxidation, peracid --- Epoxide -> Alkene --- Alkyl-OH -> Alkyl-H --- Radical reduction(C-OR) --- Ozonolysis --- RC-Alkene/Alkene+O3 --- Dehydrochlorination -> Vinyl-OR --- Baeyer-Villiger --- EC-Enone/CarboxEster+NaBH4
Reagents: BH4-Na+ --- O3 --- Me2S --- Orthoformate --- AlH4-Li+ --- DMSO, (COCl)2 --- HCl, H2O --- Cr2O7·2PyH (PDC) --- Hydroxide, potassium --- MeSO2Cl --- NEtiPr2 --- Acetonitrile (solvent) --- Perbenzoic acid, 3,5-dinitro --- HCl, H2O --- Ac2O --- Perbenzoic acid, 3-chloro --- BF3 --- AcOH --- Cr2O7·2PyH (PDC) --- HSiEt3 --- OsO4 --- O=C(CO2Me)Cl --- HSnBu3 --- HCl, H2O --- AIBN --- DMAP

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