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Total synthesis of Quadrone :
Reference: Burke, S. D.; Murtiashaw, C. W.; Saunders, J. O.; Dike, M. S. J. Am. Chem. Soc. 1982, 104, 872. DOI
Keywords: Enone → Allyl-OH • Jones oxidation • Aldehyde → CarboxAcid • CarboxAcid → CarboxCl • Alkene cleavage • Ketone → Ketal • Wharton transposition • Aldehyde → Enol-R • Alkene cleavage • Jones oxidation • Ketal → Ketone • Aldehyde → CarboxAcid • CarboxAcid → CarboxEster • Claisen-Enol ether • Si-Vinyl+Acyl-X • Friedel-Crafts Acylation, Ene • Enone epoxidation, nucleophilic • Claisen-Enol ether • Li-Vinyl+Ketone • Enone+Li-R • Enone-β-OR → Enone • Stork-Danheiser • Hydrogenation alkene • CompRed-Alkene/Aldehyde+H2 • Aldol-Na → Enone • Aldehyde enamine+Enone • Enone+Enamine • ConjAdd Enamine • Lemieux-Johnson oxidation • CompOx-Alkene/Enone+OsO4 • Mechanism • CompNu-Si-Vinyl/Alkene+Acylium •
Reagents: Hg(OAc)2 • Hg(OAc)2 • Vinyl-OR • Vinyl-Li • AlH4-Li+ • CrO3, H2SO4 (Jones) • Oxalyl chloride • TiCl4 • OsO4, NaIO4 • NMO • Hydroxide, sodium • 18-cr-6 • Glycol • Hydroperoxide, tbutyl • Hydrazine • Acetic acid • Acetate, potassium • OsO4, NaIO4 • H2, Pd • CrO3, H2SO4 (Jones) • Diazomethane • Vinyl-OR • Morpholine •

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