Total synthesis of Progesterone (Stork) New:
| Reference: | Stork, G.; McMurry, J. E. J. Am. Chem. Soc. 1967, 89, 5464-5465. DOI |
| Reactions: | Ketone → Alkyl-OH • CompRed-Ketone/Enone+M-H • CarboxEster → Alkyl-OH • Alkyl-OH → Alkyl-Cl • Enone enolate+Alkyl-X • Deconjugative alkylation • Benzyl-X+Enolate • Hydrogenation Enone • N-OR → N-H • Imine → Ketone • Aldol-Na → Enone • Bicyclo(440) • Retro-Claisen • ConjReduct-Alkylation • ConjReduct Enone • Ketone enolate+Me-I • Aldol-Na → Enone • Bicyclo(440) • Ketal → Ketone • Enone → Ketal • Ketone → Alkyl-OH • Mg-Alkyl+Ketone • Dehydration → Ene • Ketal → Enone • Alkene → Diol-1,2 • CompOx-Alkene/Enone+OsO4 • O-H → O-SO2Me • CompNu-O-H/O-H+RSO2X • Semipinacol • Steroid synthesis • |
| Reagents: | AlH4-Li+ • SOCl2 • Wieland-Miescher • NaH • BH4-Na+ • H2, Pd • H2, RaNi • NaOMe • Hydroxide, sodium • Li°/NH3 • MeI • Hydroxide, sodium • Glycol • CrO3·Py2 (Collins) • Me-MgBr • SOCl2 • HCl, MeOH • OsO4 • Sulfonyl chloride, methane • KOtBu • |