Total synthesis of Daunamycinone, 11-Deoxy:
| Reference: | Hauser, F. M.; Mal, D. J. Am. Chem. Soc., 1983, 105, 5688. DOI |
| Reactions: | Diels-Alder, EnoateEster • Bicyclo(222) • Nitrile → CarboxAcid • Alkyl-X → Alkyl-CN • Cu-Me+CarboxCl • CarboxCl+Cu-R • Aldol-Acid → Enone • Cyclohexenone • Bicyclo(440) • Mechanism • ConjAdd-Acylation (intram) • Alkene cleavage • O-C(O)R → O-H • Naphthalene synthesis • Anthraquinone synthesis • Alkyl-OH → Aldehyde • CarboxAcid → CarboxCl • CarboxEster → Alkyl-OH • |
| Reagents: | AlH4-Li+ • Sulfonyl chloride, methane, Py • Cyanide, sodium • Hydroxide, potassium • RuO4 • Periodate, sodium • SOCl2 • Me-Cuprate • Hydroxide, sodium • CrO3·Py2 (Collins) • HCl, THF • DMF (solvent) • O2 • Hydroquinone • Acrylate • Cyclohexadiene • DMF (solvent) • LiOtBu • |