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Total synthesis of Reserpine (Woodward):
Reference: Woodward, R. B.; Bader, F. E.; Bickel, H.; Frey, A. J.; Kierstead, R. W. J. Am. Chem. Soc. 1956, 78, 2023-2055; DOI; Woodward, R. B.; Bader, F. E.; Bickel, H.; Frey, A. J.; Kierstead, R. W. J. Am. Chem. Soc. 1956, 78, 2657; DOI Woodward, R. B.; Bader, F. E.; Bickel, H.; Frey, A. J.;
Kierstead, R. W. Tetrahedron 1958, 2, 1-57. DOI
Keywords: Dehydrohalogenation → Enone • CarboxAcid → CarboxEster • O-H → O-C(O)R • Amine epimerization • Mechanism • Diels-Alder, Quinone • Meerwein-Ponndorf-Verley • Lactone-5 • Enone → Allyl-OH • Bromoetherification • Furst-Plattner diaxial • Ether-5 • Bischler-Napieralski • Amine-6 • ConjAdd M-OR • Alkene → Bromohydrin • Furst-Plattner diaxial • Reductive amination, B-H • Lactam-6 • N-H → N-Alkyl • Reductive elimination - X/OR • Ketone-α-OR → Ketone • Lemieux-Johnson oxidation • Alkene cleavage • Iminium → Amine • CarboxEster → CarboxAcid • Lactone-5 • O-H → O-C(O)R • Jones oxidation • Alkyl-OH → Ketone-α-Halo •
Reagents: Quinone • Al(OiPr)3 • Br2 • NaOMe • NBS • CrO3, H2SO4 (Jones) • Acetic acid • Zn° • Acetic acid • Diazomethane • Acetic anhydride • OsO4 • Periodic acid • POCl3 • BH4-Na+ • Hydroxide, potassium • Carbodiimide • NaOMe • Pyridine • BH4-Na+

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