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Total synthesis of Neothiobinupharidine:
Reference: Jansen, D. J.; Shenvi, R. A. J. Am. Chem. Soc. 2013, 135, 1209-1212. DOI
Keywords: EnolSilane → Ketone enolate • Ketone → Imine • Li-Aryl+CarboxAmide • CarboxAmide+Li-R • Reductive amination, B-H • ConjReduct-Alkylation • Pd-enolate allylation(asym) • Tsuji-Trost allylation • Beckman rearrangement • RCM → Ring-N • Amine → AmineOxide • Polonovsky reaction • N-H → N-Alkyl • Si-Allyl → H-Allyl • Iminium+S-R • Reductive amination, B-H • Lactam-6 •
Reagents: HSiH2Ph • NaOtBu • MeLi • Hydroxide, sodium • NH2OH • TsCl, Py • CuCl • Pd2(dba)3 • BINAP • LiNiPr2 • Grubbs II • Acetic acid, trifluoro • BH(OAc)3-Na+ • Perbenzoic acid, 3-chloro • Acetic anhydride, trifluoro • Sulfide, sodium • BH4-Na+ • DMSO (solvent) •

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