Total synthesis of Bilobalide (Corey):
| Reference: | Corey, E. J.; Su, W. J. Am. Chem. Soc. 1987, 109, 7534. DOI |
| Reactions: | Epoxidation, peracid • Epoxide → Alkene • Alkyl-OH → Alkyl-H(2°) • Radical reduction(C-OR) • Ozonolysis • CompOx-Alkene/Alkene+O3 • Dehydrohalogenation → EnolEther • Baeyer-Villiger • Enone → Allyl-OH • CompRed-Ketone/CarboxEster+M-H • CarboxEster enolate+Ynone • Ynone+Enolate • Bicyclo(430) • Aldehyde → Acetal(Me) • CarboxEster → Alkyl-OH • Alkyl-OH → Aldehyde • Acetal → Acetal(Me) • Aldehyde → CarboxAcid • Lactone-5 • Epoxide → Diol • O-H → O-C(O)R • Alkene → Diol-1,2 • |
| Reagents: | BH4-Na+ • O3 • Me2S • TsOH • AlH4-Li+ • DMSO, (COCl)2 (Swern) • HCl, H2O • Cr2O7·2PyH (PDC) • Hydroxide, potassium • Sulfonyl chloride, methane • NEtiPr2 • Acetonitrile (solvent) • Perbenzoic acid, 3,5-dinitro • HCl, H2O • Acetic anhydride, DMAP • BF3·OEt2 • Acetic acid • Cr2O7·2PyH (PDC) • HSiEt3 • OsO4 • O=C(CO2Me)Cl • HSnBu3 • HCl, H2O • AIBN • Orthoformate • Perbenzoic acid, 3-chloro • |