Total synthesis of Equilenin (Johnson):
| Reference: | Johnson, W. S.; Peterson, J. W.; Gutsche, C. D. J. Am. Chem. Soc. 1949, 69, 2942-2955. DOI |
| Reactions: | Decarboxylation β-keto acid • Mechanism • CarboxEster enolate+Ketone • Stobbe condensation • Claisen acylation, formate • Ketone enolate+CarboxEster • Isoxazole synthesis • Nitrile+CarboxEster enolate • Cyclopentenone • Isoxazole → Nitrile • Decarboxylation • Hydrogenation Alkene • O-Me → O-H (phenol) • Steroid synthesis • Nitrile anion+Alkyl-X • CarboxEster → CarboxAcid • |
| Reagents: | NaOMe • Formate, methyl • NH2OH • Acetic acid • KOtBu • MeI • Hydroxide, barium • HCl, H2O • H2, Pd • HCl • Succinate • KOtBu • HCl, H2O • |