Total synthesis of Estrone (Grieco):
| Reference: | Grieco, P. A.; Takigawa, T.; Schillinger, W. J. J. Org. Chem. 1980, 45, 2247. DOI |
| Reactions: | CarboxEster → Alkyl-OH • CarboxAcid → CarboxEster • Selenide → Selenoxide • Selenoxide-Ei → Ene • CarboxEster enolate+Alkyl-X • Alkyl-X+Enolate • Baeyer-Villiger • Hydrogenation alkene • Dehydrohalogenation → Ene • Bicyclo(221) • Alkyl-OH → Alkyl-H • Steroid synthesis • Diels-Alder, Intram, o-Xylylene • Cyclohexane • Bicyclo(440) • Bicyclo(430) • Electrocyclic-4π • Ketal → Ketone • Jones oxidation • Alkyl-OH → Ketone • O-Me → O-H (phenol) • O-H → O-SO2Me • Alkyl-X → Alkyl-H • Alkyl-OH → Alkyl-SeR • CarboxEster → Alkyl-OH • |
| Reagents: | DBU • LiNiPr2 • AlH4-Li+ • Sulfonyl chloride, methane • BH(Et)3-Li+ • HCl, H2O • H2O2, NaOH • Diazomethane • H2, Pt • AlH4-Li+ • Selenocyanate, o-nitrophenyl • PBu3 • H2O2 • CrO3, H2SO4 (Jones) • B(Br)3 • DMF (solvent) • |