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Total synthesis of Equilenin:
Reference: Bachmann, W. E.; Cole, W.; Wilds, A. L. J. Am. Chem. Soc. 1939, 61, 974-975. DOI
Keywords: CarboxEster → CarboxAcid • CompE+-CarboxEster/CarboxEster+KOH • EnoateEster ConjReduct • CarboxAcid → CarboxEster • Claisen acylation, oxalate • Ketone enolate+CarboxEster • Decarbonylation • Acetoacetic ester synthesis • Dehydration → Enoate • Diazoketone • Arndt-Eistert • Dieckmann • CarboxEster enolate+CarboxEster • Decarboxylation • Reformatsky • CarboxEster enolate+Ketone • Steroid synthesis •
Reagents: Oxalate • MeI • NaOMe • Bromoacetate • SOCl2 • Hydroxide, potassium • Na(Hg) • Diazomethane • Hydroxide, sodium • SOCl2 • Diazomethane • Ag2O • NaOMe • HCl • NaOMe •

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