Total synthesis of Desogestrel:
| Reference: | Corey, E. J.; Huang, A. X. J. Am. Chem. Soc. 1999, 121, 710. DOI |
| Reactions: | Mitsunobu → Hydrazine • O-SiMe2tBu → O-H • O-C(O)R → O-H • O-H → O-SiMe2tBu • Claisen acylation, carbonate • Ketone enolate+Carbonate • ConjReduct Enone • KetoEster dianion+Alkyl-X • Alkyl-X+Enolate • Friedel-Crafts Vinylation • Cyclohexene • Bicyclo(440) • Birch reduction • Ce-Alkynyl+Ketone • Ketone+Ce-R • Steroid synthesis • Mechanism • Mechanism • Ketal(thio) → CH2 • Ketone → CH2 • Alkyl-OH → Ketone • CarboxEster → Alkyl-OH • Enone → Ketal(thio) • O-SiMe2tBu → O-H • Diazene rearrangement • Allyl-OR → Allyl-H • |
| Reagents: | Hydrazine, tosyl • AlHiBu2 • O=C(OR)2 • NaH • Acetic acid, trifluoro • Carbonate, sodium • SiMe2tBu-Cl • AlH4-Li+ • Li°/NH3 • HF • Thiol, (CH2)2-SH • BF3·OEt2 • Li°/NH3 • Dess-Martin • Alkynyl-CeX2 • PPh3, DEAD • BuLi(n) • Imidazole • HMPA (solvent) • |