Total synthesis of Equilenin (Bachmann):
| Reference: | Bachmann, W. E.; Cole, W.; Wilds, A. L. J. Am. Chem. Soc. 1939, 61, 974-975. DOI |
| Reactions: | CarboxEster → CarboxAcid • CompE+-CarboxEster/CarboxEster+H2O • Claisen acylation, oxalate • Ketone enolate+CarboxEster • Decarbonylation • Acetoacetic ester synthesis • KetoEster enolate+Alkyl-X • Dehydration → Enoate • Diazoketone • CarboxCl → Diazoketone • Arndt-Eistert • Diazoketone → Ketene • Ketene+Alcohol • Dieckmann • CarboxEster enolate+CarboxEster • Cyclopentanone • Decarboxylation β-keto acid • Reformatsky • CarboxEster enolate+Ketone • Steroid synthesis • EnoateEster ConjReduct • CarboxEster → CarboxAcid • CarboxAcid → CarboxEster • CarboxAcid → CarboxCl • |
| Reagents: | Oxalate • MeI • NaOMe • CH2=C(OLi)(OR) • Bromoacetate • SOCl2 • Hydroxide, potassium • Na(Hg) • Diazomethane • Hydroxide, sodium • SOCl2 • Diazomethane • Ag2O • NaOMe • HCl, AcOH • HOMe (react) • NaOMe • |