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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: Pd/H-Alkynyl+Vinyl-X • Ketone enamine+Aldehyde • Aldol-enamine → Enone • Alkyl-OH → Aldehyde • CompOx-Alkyl-OH/Sulfide+CrO3 • Acetal → Acetal • Wohl-Ziegler bromination • 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-OR • Oxaziridine+Enolate • CarboxEster enolate oxidation • CarboxEster enolate+Ketone • Epoxide → Diol • Lactone-5 • Lactol → Lactone • Lactone-5 • CompOx-Lactol/Alkyl-OH+I2 • CompE+-Ketone/Lactone+Enolate • Hydroboration Alkyne • CompRed-Alkyne/Alkene+M-H • Enone epoxidation, nucleophilic • CompOx-Enone/Alkene+ROOH • Protecting group - CarboxAcid • Baeyer-Villiger • Lactone-5 • Ketene Cycloaddition • Cyclobutane • Cyclopentene • Acetal(thio) → Acetal • Alkene isomerization • Ketone → EnolTriflate • B-Vinyl → H-Vinyl • Alkyne → Ene-cis (B-H) • Orthoester → CarboxAcid • CarboxAcid → CarboxCl • Acetal → Acetal(thio) •
Reagents: HCl • CuCN • SiMe3-Cl • TiCl4 • LiNiPr2 • Tf2NPh • Pd(PPh3)4 • CuI • NH2Pr • BH(Cy)2 • Acetic acid • H2O2 • HCl • TiCl4 • CrO3Cl·PyH (PCC) • 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 •

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