Total synthesis of 11-Oxo-Equilenin:
| Reference: | Posner, G. H.; Chapdelaine, M. J.; Lentz, C. M. J. Org. Chem. 1979, 44, 3661. DOI |
| Reactions: | Ketal → Ketone • Cu-Aryl+Enone • Enone+Cu-Aryl • ConjAdd-Alkylation • Mg-R → Cu-R • Ketone enolate+Alkyl-X • Bromoacetate+Enolate • Bromoacetate+Enolate • Friedel-Crafts Acylation • Cyclohexanone • Bicyclo(430) • Steroid synthesis • CarboxEster → CarboxAcid • Ketone → Ketal • |
| Reagents: | Bromoacetate • HMPA (solvent) • Glycol • HF • Hydroxide, sodium • |