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Total synthesis of Bilobalide:
Reference: Corey, E. J.; Su, W. J. Am. Chem. Soc. 1987, 109, 7534. DOI
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 • Dehydrohalogenation -> Vinyl-OR • Baeyer-Villiger • EC-Enone/CarboxEster+B-H •
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 • DMAP • Perbenzoic acid, 3-chloro • BF3 • Acetic acid • Cr2O7·2PyH (PDC) • HSiEt3 • OsO4 • O=C(CO2Me)Cl • HSnBu3 • HCl, H2O • AIBN •

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