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Total synthesis of Mesembrine (Keck):
Reference: Keck, G. E.; Webb, R. R. J. Org. Chem. 1982, 47, 1302. DOI
Keywords: O-H → O-C(O)R • CarboxAcid → CarboxHydroxamate • N-OH → N=O • Ketone → Ketal • Ketal → Ketone • Claisen-Ireland • Diels-Alder, Nitroso • Nitroso Cycloaddition • Li-Aryl+Ketone • Enone-β-OR+Li-R • Enone-β-OR → Enone • Stork-Danheiser • Nitroso ene • Lactam-5 • Retro-Diels-Alder → Nitroso • Mechanism • N-OR → N-H • Radical reduction(C-Br) • Alkyl-X → Alkyl-H(2°) • N-H → N-Me • Alkene → Bromohydrin • Alkyl-OH → Ketone • CarboxAmide → Amine • Amine-5 • Enone → Allyl-OH •
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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