Total synthesis of 3-Methoxy-Estra-1,3,5(10)-triene:
| Reference: | Bryson, T. A.; Pye, W. E. J. Org. Chem. 1977, 42, 3214 DOI |
| Reactions: | Selenide → Selenoxide • Claisen-EnolEther • 2,3-Sigmatropic Ylide-N/O/S • Ammonium ylide • Selenoxide-Ei → Ene • Hydroboration → Alkyl-B • Alkyl-X → Alkyl-SeR • Selenolate+Alkyl-X • Steroid synthesis • Borane Carbonylation • Cyclohexanone • Bicyclo(430) • Friedel-Crafts Alkylation • Cyclohexene • Bicyclo(440) • Hydrogenation alkene • Aldehyde → Alkyl-OH • O-H → O-SO2Me • Enone → Allyl-OH • CyanoAmine • CyanoAmine → Ketone • Alkene isomerization • |
| Reagents: | Allyl-Cl • KOtBu • CuSO4 • HCl, H2O • AlH4-Li+ • Vinyl-OR • Hg(OAc)2 • AlH4-Li+ • Sulfonyl chloride, methane, NEt3 • Selenolate, o-nitrophenyl • H2O2 • BH2(Thexyl) • HCl, MeOH • H2, Pd • CO • H2O2 • |