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Total synthesis of Brunsvigine:
Reference: Sha, C.-K.; Hong, A.-Wei.; Huang, C. M. Org. Lett. 2001, 3, 2177.
Keywords: Luche reduction --- Enone -> Allyl-OH --- Luche reduction --- Enone -> Allyl-OH --- N-SO2R -> N-H --- Acetal -> Diol --- CarboxAmide(Weinreb)+Li-Vinyl --- Li/I -> Li-Vinyl --- Amine-5 --- Pictet-Spengler --- Mechanism --- EC-Vinyl-I/Weinreb amide+Li-R --- Cu-Aryl+Allyl-OAc --- Enone -> Enone-α-Halo --- Mitsunobu -> Ester --- Allyl-OH -> Allyl-OAc(2°) --- Mitsunobu -> Amine --- Allyl-OH -> Allyl-NR2(2°) --- Stereoconvergent
Reagents: I2, Py --- BH4-Na+, CeCl3 --- Benzoic acid, p-nitro --- Hydroxide, sodium --- Weinreb acetamide --- DIAD --- Vinyl-Li --- BuLi(n) --- BH4-Na+, CeCl3 --- Piv-Cl --- Aryl-MgX --- CuI --- Na°/Naphth --- CH2=NMe2+I- --- DMF (solvent) --- HCl, MeOH --- PPh3, DEAD

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