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Total synthesis of Desogestrel:
Reference: Corey, E. J.; Huang, A. X. J. Am. Chem. Soc. 1999, 121, 710. DOI
Keywords: Mitsunobu → Hydrazine • Allyl-OR → Allyl-H • O-SiMe2tBu → O-H • O-H → O-SiMe2tBu • CarboxEster → Alkyl-OH • O-SiMe2tBu → O-H • Enone → Ketal(thio) • Ketal(thio) → CH2 • Ketone → CH2 • Alkyl-OH → Ketone • Claisen acylation, carbonate • Ketone enolate+Carbonate • ConjReduct Enone • Ketoester dianion+Alkyl-X • Alkyl-X+Enolate • Friedel-Crafts Vinylation • Birch reduction • Ce-Alkynyl+Ketone • Ketone+Ce-R • Steroid synthesis • Mechanism • Mechanism •
Reagents: Hydrazine, tosyl • AlHiBu2 • HMPA (solvent) • 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 • Dess-Martin • DEAD •

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