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Total synthesis of Quadrone:
Reference: Danishefsky, S.; Vaughan, K.; Gadwood, R. C.; Tsuzuki, K. J. Am. Chem. Soc. 1981, 103, 4136. DOI
Keywords: Ketone → Ketal • Hydroboration alkene • Finkelstein reaction • Alkyl-OH → Alkyl-Br • Ketal → Ketone • CarboxAcid → CarboxEster • Ketone → Ketal • Alkyl-X → Alkyl-I • Finkelstein reaction • Ketal → Ketone • CarboxEster → CarboxAcid • Ketone → Ketone-α-SeR • Selenoxide-Ei → Enone • Ketone → Enone • Ketene acetal+β-DicarbonylEnone • Enone+EnolSilane • ConjAdd EnolSilane • Aldol-Li → Aldol • Enone enolate+Aldehyde • Hydrogenation Enone • CompRed-Alkene/Ketone+B-H • Aldol-Na → KetoEsterEnone • Knoevenagel condensation • Decarboxylation • Lactone-6 • ConjAdd-Alkylation • Cu-Vinyl+Enone • CarboxEster enolate+Alkyl-X •
Reagents: Glycol • TsOH • BH3 • Sulfonyl chloride, methane • Bromide, lithium • NaOMe • Ketene acetal • TiCl4 • HCl • Diazomethane • Glycol • Iodide, sodium • LiN(SiMe3)2 • Hydroxide, potassium • SePh-Cl • H2O2 • LiNiPr2 • Formaldehyde • H2, Pt • H2O2, NaOH • HMPA (solvent) • Vinyl-MgX • CuI·PBu3 • Allyl-Br •

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