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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
Keywords: Selenide → Selenoxide • Claisen-Enol ether • 2,3-Sigmatropic Ylide-N/O/S • Ammonium ylide • Selenoxide-Ei → Ene • Hydroboration alkene • Alkyl-X → Alkyl-SeR • Selenolate+Alkyl-X • Steroid synthesis • Borane Carbonylation • Cyclohexanone • Friedel-Crafts Alkylation • Cyclohexene • Hydrogenation alkene • Aldehyde → Alkyl-OH • O-H → O-SO2R • Enone → Allyl-OH • CyanoAmine • CyanoAmine → Ketone • Alkene isomerization •
Reagents: Allyl-Cl • KOtBu • CuSO4 • HCl • AlH4-Li+ • Vinyl-OR • Hg(OAc)2 • AlH4-Li+ • Sulfonyl chloride, methane, NEt3 • Selenolate, o-nitrophenyl • H2O2 • BH2(Thexyl) • HCl • H2, Pd • CO • H2O2

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