Total Syntheses

Reaction scheme for total synthesis of the natural product Deoxy-Estrone
Total synthesis of Deoxy-Estrone:
Reference:Nicolaou, K. C.; Barnette, W. E. Chem. Commun 1979, 1119. DOI
Reactions:ConjAdd-Alkylation • Bromoacetate+Enolate • Cu-Vinyl+Enone • Enone+Cu-Vinyl • ConjAdd Cu-Vinyl • Mg-R → Cu-R • Li-Sulfone+Alkyl-X • Alkyl-X+Li-R • Chelotropic, SO2 • Diels-Alder, Intram, o-Xylylene • Cyclohexane • Bicyclo(440) • Bicyclo(430) • Steroid synthesis • Ketone → Ketal • CarboxEster → Alkyl-OH • O-H → O-SO2Ar • Ketal → Ketone •
Reagents:Vinyl-MgX • CuI • Bromoacetate • Glycol • TsOH • AlH4-Li+ • TsCl, Py • LiCHR-Sulfonyl • KH • Acetic acid •