Total synthesis of Progesterone (Boeckman):
| Reference: | Boeckman, R. K. J. Am. Chem. Soc. 1974, 96, 6179–6181. DOI |
| Reactions: | Ketal → Ketone • Semipinacol • Cyclopentane • Bicyclo(430) • ConjReduct-Michael • Ketone enolate+Enone • ConjReduct Enone • Aldol-K → Enone • Robinson annulation, Stork • Cyclohexenone • Bicyclo(440) • ConjReduct-Alkylation • ConjReduct Enone • Ketone enolate+Me-I • Aldol-K → Enone • Cyclohexenone • Bicyclo(440) • Alkene → Diol-1,2 • O-H → O-SO2Me • CompNu-O-H/O-H+RSO2X • |
| Reagents: | Li°/NH3 • Hydroxide, potassium • Li°/NH3 • MeI • Hydroxide, potassium • Methyl vinyl ketone • Vinyl-SiR3 • OsO4 • Sulfonyl chloride, methane • KOtBu • |