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Total synthesis of Mesembrine:
Reference: Keck, G. E.; Webb, R. R. J. Org. Chem. 1982, 47, 1302. DOI
Keywords: Enone -> Allyl-OH • O-H -> O-C(O)R • CarboxAcid -> CarboxHydroxamate • N-OH -> N=O • N-H -> N-Me • Radical reduction(C-Br) • Alkyl-OH -> Ketone • Ketone -> Ketal • CarboxAmide -> Amine • Ketal -> Ketone • N-OR -> N-H • Claisen-Ireland • Diels-Alder, Nitroso • Nitroso Cycloaddition • Li-Aryl+Ketone • Enone-β-OR+Li-R • Enone-β-OR -> Enone • Stork-Danheiser • Bromohydrin • Nitroso ene • Lactam-5 • Retro-Diels-Alder, nitroso • Mechanism •
Reagents: LiNiPrCy • SiMe2tBu-Cl • Aryl-Li • BH4-Na+ • Acetic anhydride, Py • SOCl2 • NH2OH • Periodate • TiCl3 • MeI • NBS • HSnBu3 • CrO3Cl·PyH (PCC) • Glycol • AlH4-Li+ • Carbonate, sodium • AIBN •

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