Total synthesis of Ouabain Model:
| Reference: | Jung, M. E.; Piizzi, G. Org. Lett. 2003, 5, 137. DOI |
| Reactions: | Enone → Ketal • Ketal → Enone • Robinson annulation, ketoester • KetoEster enolate+Enone • Cyclohexenone • Bicyclo(440) • Enone epoxidation, nucleophilic • Enone epoxidation, nucleophilic • Orthoester • Epoxide reduction • Ketone-α-OR → Ketone • Ketone → Enone • Ketone → Alkyl-OH • CarboxEster → Alkyl-OH • Ketone → Enone • |
| Reagents: | Methyl vinyl ketone • KOtBu • Glycol • AlH4-Li+ • H2SO4 • H2O2, NaOH • H2O2, NaHCO3 • HgCl2 • BH(Et)3-Li+ • Orthoformate • Al(Hg) • SeO2 • |