Total synthesis of Quadrone (Burke):
| Reference: | Burke, S. D.; Murtiashaw, C. W.; Saunders, J. O.; Dike, M. S. J. Am. Chem. Soc. 1982, 104, 872. DOI |
| Reactions: | Alkene cleavage • Wharton transposition • Claisen-EnolEther • Si-Vinyl+CarboxCl • Friedel-Crafts Acylation, Ene • Cyclopentenone • CompNu-Si-Vinyl/Alkene+Acylium • Spiro(54) • Enone epoxidation, nucleophilic • Claisen-EnolEther • Li-Vinyl+Ketone • Enone+Li-R • Enone-β-OR → Enone • Stork-Danheiser • Hydrogenation alkene • CompRed-Alkene/Aldehyde+H2 • Aldol-Na → Enone • Cyclohexenone • Bicyclo(321) • Aldehyde enamine+Enone • Enone+EnAmine • ConjAdd EnAmine • Lemieux-Johnson oxidation • CompOx-Alkene/Enone+OsO4 • Mechanism • Alkene cleavage • Aldehyde → Enol-R • Ketone → Ketal • CompE+-Ketone/Enone+glycol • Ketone → Hydrazone • Enone → Allyl-OH • Jones oxidation • Aldehyde → CarboxAcid • CarboxAcid → CarboxCl • Jones oxidation • Ketal → Ketone • Aldehyde → CarboxAcid • CarboxAcid → CarboxEster • O-H → O-Vinyl • |
| Reagents: | Hg(OAc)2 • Hg(OAc)2 • Vinyl-OR • Vinyl-SiR3 • Vinyl-Li • AlH4-Li+ • CrO3, H2SO4 (Jones) • Oxalyl chloride • TiCl4 • OsO4, NaIO4 • NMO • Hydroxide, sodium • 18-crown-6 • Glycol • Hydroperoxide, tbutyl • Hydrazine • Acetic acid • Acetate, potassium • OsO4, NaIO4 • H2, Pd • CrO3, H2SO4 (Jones) • Diazomethane • Vinyl-OR • Morpholine • |