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Total synthesis of Saudin:
Reference: Boeckman, R. R. Jr.; Ferreira, M. R.; Mitchell, L. H.; Shao, P.; Neeb, M. J.; Fang, Y.. Tetrahedron 2011, 67, 9787-9808. DOI
Keywords: O-H → O-SiPh2tBu • O-H → O-Tf • CarboxEster → CarboxAcid • CarboxAcid → CarboxEster • Williamson esterification • O-SiPh2tBu → O-H • Hydroboration alkene • Alkyl-OH → Aldehyde • Aldehyde → CarboxAcid • Lactone-6 • O-H → O-C(O)R • O-C(O)R → O-H • Alkyl-OH → Aldehyde • Aldehyde → CarboxAcid • Ketone → EnolCarboxylate • CarboxEster → CarboxAcid • ConjAdd Enamine • Michael(asym) Enamine • Aldol-enamine → Enone • Robinson annulation, enamine • Enone enolate+Alkyl-X • Alkyne → Ene-trans • Li-Alkynyl+Aldehyde • Aldehyde+Li-R • Claisen-Enol ether • Ketone → Ketal(Me) • Epoxidation, peracid • Li-Aryl+Lactone • Lactone+Li-R • Epoxide → Diol • Lactone enolate+Alkyl-X • CarboxEster epimerization • Lactone-5 •
Reagents: SiPh2tBu-Cl • BuLi(n) • Formaldehyde • AlH4-Li+ • Tf2O • ZnCl2 • Acetic acid • Hydroxide, potassium • Sulfate, dimethyl • KN(SiMe3)2 • HMPA (solvent) • TiCl4 • AlMe3 • Fluoride, R4N+ • Orthoformate • TsOH • BH-BBN • NaBO3 • DMSO, (COCl)2 (Swern) • Chlorite, sodium • Perbenzoic acid, 3-chloro • HCl • Furyl-Li • DMAP • BF3·OEt2 • Carbonate, potassium • DMSO, (COCl)2 (Swern) • Chlorite, sodium • Acetic anhydride, trifluoro • Acetate, sodium • LiTMP • HMPA (solvent) • MeI • LiNiPr2 • Hydroxide, potassium • SiMe3-OTf •

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