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Total synthesis of Daunamycinone, 11-Deoxy:
Reference: Hauser, F. M.; Mal, D. J. Am. Chem. Soc., 1983, 105, 5688. DOI
Keywords: Diels-Alder, EnoateEster • CarboxEster → Alkyl-OH • Alkene cleavage • CarboxAcid → CarboxCl • O-C(O)R → O-H • Alkyl-OH → Aldehyde • Nitrile → CarboxAcid • Alkyl-X → Alkyl-CN • Cu-Me+CarboxCl • CarboxCl+Cu-R • Aldol-H+ → Enone • Mechanism • ConjAdd Enolate •
Reagents: AlH4-Li+ • Sulfonyl chloride, methane • Cyanide, sodium • Hydroxide, potassium • RuO4 • Periodate, sodium • SOCl2 • LiCuMe2 • Hydroxide, sodium • CrO3·Py2 (Collins) • HCl, THF • DMF (solvent) • O2 • Hydroquinone • Acrylate • Cyclohexadiene • DMF (solvent) • LiOtBu •

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