image

Total synthesis of Ginkgolide B:
Reference: Corey, E. J.; Kang, M. C.; Desai, M. C.; Ghosh, A. K.; Houpis, I. N. J. Am. Chem. Soc. 1988, 110, 649-651. DOI
Keywords: Ketone → EnolTriflate • Hydroboration Alkyne • Alkyne → Ene-cis • Orthoester → CarboxAcid • Pd-Sonogashira • Ketone enamine+Aldehyde • Aldol-enamine → Enone • Acetal → Acetal(thio) • Alkyl-OH → Aldehyde • CompOx-Alkyl-OH/Sulfide+CrO3 • Acetal(thio) → Aldehyde • Acetal(thio) → Acetal • Acetal → Acetal • Allylic oxidation → Enone • Kornblum oxidation • O-H → O-SiMe2tBu • Alkene → Diol-1,2 • O-SiMe2tBu → O-H • Cu-Alkyl+Enone • Enone+Cu-R • ConjAdd-Silylation • ConjAdd Cu-R • Mukaiyama Aldol • Aldol-Si • Lactone → Lactone-α-OH • CarboxEster enolate+Ketone • Epoxide → Diol • Lactol → Lactone • Lactone-5 • CompOx-Lactol/Alkyl-OH+I2 • CompE+-Ketone/Lactone+Enolate • CompRed-Alkyne/Alkene+B-H • Enone epoxidation, nucleophilic • Protecting group - CarboxAcid • CarboxAcid → CarboxCl • Baeyer-Villiger • Lactone-5 • Ketene Cycloaddition • Cyclobutane •
Reagents: HCl • CuCN • SiMe3-Cl • TiCl4 • LiNiPr2 • Tf2NPh • Pd(PPh3)4 • CuI • NH2Pr • BH(Cy)2 • Acetic acid • H2O2 • HCl • TiCl4 • Cr2O7·2PyH (PDC) • Periodic acid • Camphor sulfonic acid • LiNEt2 • Oxaziridine • Camphor sulfonic acid • NBS • AgNO3 • TsOH·Py • Hydroperoxide, trityl • P(OMe)3 • LiNiPr2 • Camphor sulfonic acid • SiMe2tBu-OTf • OsO4 • I2 • Carbonate, calcium • BF3·OEt2 • Oxalyl chloride • NBu3 • Hydroperoxide, trityl • Hydroxide, sodium •

Syntheses Home