Total synthesis of 16,17-Dehydro-Progesterone:
| Reference: | Johnson, W. S.; Semmelhack, M. F.; Sultanbawa, M . U. S.; Dolak, L. A. J. Am. Chem. Soc. 1968, 90, 2994-2996. DOI |
| Reactions: | Cationic cyclization • Cyclohexene • Cyclohexane • Bicyclo(440) • Aldol-K → Enone • Cyclopentene • Bicyclo(430) • Mechanism • Steroid synthesis • Alkene cleavage • Criegee oxidation • O-H → O-SO2Ar • Alkyl-X → Alkyl-Br • Li-Alkynyl+Alkyl-X • Alkyne → Ene-trans • O-Bn → O-H • Alkyl-OH → Alkyl-Br • Ketone → Ketal • Claisen acylation, carbonate • Ketone enolate+Carbonate • Acetoacetic ester synthesis • Decarboxylation β-keto acid • CarboxEster → CarboxAcid • Aldol-Na → Enone • Ketone+Li-Alkyl • Li-Me+Ketone • |
| Reagents: | SnCl2 • Hydroxide, potassium • Alkynyl-Li • TsCl • Bromide, lithium • Glycol • O=C(OR)2 • NaH • NaOEt • Hydroxide, barium • HCl, H2O • Hydroxide, sodium • Me-Li • OsO4 • Pb(OAc)4 • |