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Total synthesis of Rhazinicine:
Reference: Beck, E. M.; Hatley, R.; Gaunt, M. J. Angew. Chem. Int. Ed. 2008, 120, 3046–3049. DOI
Keywords: CarboxEster → CarboxAcid • CarboxAcid → CarboxAnhydride • CarboxAcid → CarboxAmide • Nitro → Amine • Hydrogenation alkene • Si-Aryl → H-Aryl • Lactam-9 • Wittig-alkyl+Ketone • C-H functionalization • Pd/H-Aryl+B-B • Suzuki coupling • Pd/B-Aryl+Aryl-X • C-H functionalization • Aryl-H → Aryl-Pd • Pd-Heck coupling • Lactam-6 • N-Boc → N-H • CarboxAcid → CarboxCl •
Reagents: PPh3=CH-Me • KOtBu • Hydroxide, potassium • Acetic anhydride • Pyridine, 2,6-di-tBu • B2(Pinacol)2 • Pd(OAc)2 • LiN(SiMe3)2 • Oxalyl chloride • DMF (solvent) • Acetic acid, trifluoro • Pd/C • AlCl3 • Pyridinium, 2-halo •

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