image

Total synthesis of Morphine:
Reference: Taber, D. F.; Neubert, T. B.; Rheingold, A. L. J. Am. Chem. Soc. 2002, 124, 12416 DOI
Keywords: Ketone → Ketal • Azide → Amine • Ketal → Ketone • Enone → Allyl-OH • ArylO-Me → ArylO-H • Ether-5 • N-H → N-C(O)OR • Epoxidation, W • Allyl-OH → Enone • ArylO-Me → ArylO-H • Mitsunobu → Azide • Alkyl-OH → Alkyl-N3 • Resolution • Selenoxide-Ei → Allyl-OR • Epoxide → Allyl-OH • Birch reduction • Ketoester dianion+Alkyl-X • Alkyl-X+Enolate • Claisen acylation, carbonate • Ketone enolate+Carbonate • Aryl-Br → Aryl-OMe • ArylO-H → ArylO-R • Decarboxylation Krapcho • N-H → N-Alkyl • Furst-Plattner (anti) • N-SO2R → N-H • Ozonolysis • N-C(O)OR → N-Me • Aldehyde enolate+Alkyl-X • Amine-6 • Alkyl-X+Enolate • Aldol-K → Enone • Mechanism • Carbene insertion •
Reagents: Carbonate, potassium • Collidine • Na°, ROH • HCl, H2O • O=C(OR)2 • NaOMe • LiNiPr2 • Allyl-Br • Chloride, lithium • TsOH • Orthoformate • BH(sBu3)-Li+ • Azide, diphenylphosphoryl • AlH4-Li+ • Acetic acid • Sulfonyl chloride, benzene • Ethylene dibromide • O3 • BH4-Na+ • B(Br)3 • AlH2(OR)2-Na+ • O=C(OR)Cl • H2O2, W • Selenolate, phenyl • Periodate, sodium • MnO2 • AlH4-Li+ • B(Br)3 • PPh3, DEAD • DMSO (solvent) • Carbonate, potassium • KN(SiMe3)2 • Chiral auxiliary-Ketal •

Syntheses Home