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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 • Ketone -> Ketone-α-SeR • Selenoxide-Ei -> Enone-5 • Ketone -> Enone • Ketene acetal+β-DicarbonylEnone • Enone+Enolsilane • ConjAdd Enolsilane • Aldol-Li -> Aldol • Enone Enolate+Aldehyde • CarboxEster enolate+Alkyl-X • Hydrogenation Enone • CompRed-Alkene/Ketone+B-H • Aldol-Na -> KetoEsterEnone • Knoevenagel condensation • Decarboxylation • Lactone-6 • ConjAdd-Alkylation • Cu-Vinyl+Enone •
Reagents: Glycol • TsOH • BH3 • MeSO2Cl • Bromide, lithium • NaOMe • CH2=C(OR)(OSiR'3) • 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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