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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 • Alkene → Bromohydrin • Nitroso ene • Lactam-5 • Retro-Diels-Alder → Nitroso • Mechanism •
Reagents: LiNiPrCy • SiMe2tBu-Cl • Aryl-Li • BH4-Na+ • Acetic anhydride • SOCl2 • NH2OH • Periodate • TiCl3 • MeI • NBS • HSnBu3 • CrO3Cl·PyH (PCC) • Glycol • AlH4-Li+ • Carbonate, sodium • AIBN •

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