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Total synthesis of LL-Z1271α:
Reference: Welch, S. C.; Hagan, C. P.; White, D. H.; Fleming, W.P.; Trotter, J. W. J. Am. Chem. Soc. 1977, 99, 549. DOI
Keywords: Ketone → EnolEther • CarboxEster → CarboxAcid • O-THP → O-H • Jones oxidation • Alkyl-OH → Ketone • Ketone → Ketone-α-Halo • CarboxAcid → CarboxEster • Lactone-5 • Williamson esterification • Ketone → Ketone-α-SeR • Enal → Acetal • Meyer-Schuster Rearrangement • Lactone-6 • Ketone → Alkyl-OH • O-H → O-THP • Ketone enolate+CO2 • CarboxAcid → CarboxEster • Selenoxide-Ei → KetoEsterEnone • Aldehyde → Enal • ConjReduct-Alkylation • CarboxEster enolate+Alkyl-X • EnoateEster ConjReduct • Alkyl-X+Enolate • Robinson annulation, diketone • Ketone enamine+Enone • Enone+Enamine • Mechanism • Li-Alkynyl+Ketone • Enone+Li-R • Li/H → Li-Alkynyl • CompE+-Ketone/Lactone+Li-R • Hydrogenation Enone • Dehydrohalogenation → Enone • Ketone → Enone • Claisen acylation, formate • Ketone enolate+Formate • ConjReduct Enone • ConjReduct-Acylation • CompRed-Ketone/Enone+B-H • Mechanism •
Reagents: NaH • Chloromethyl ether • Li°/NH3 • MeI • Thiolate, propyl • CrO3, H2SO4 (Jones) • Bromine • Carbonate, calcium • Bromine • Carbonate, potassium • H2, Rh • Rh(PPh3)3Cl • NaH • Formate, ethyl • SePh-Cl • Perbenzoic acid, 3-chloro • Glycol • Alkynyl-Li • H2SO4 • Wieland-Miescher • Hydroxide, potassium • Pyrrolidine • Wieland-Miescher • BH4-Na+ • DHP • Li°/NH3 • CO2 • Diazomethane • Methyl vinyl ketone • HMPA (solvent) • HMPA (solvent) • DMF (solvent) •

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