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Total synthesis of Strychnine (Vanderwal):
Reference: Martin D. B. C.; Vanderwal C. D. Chem. Sci., 2011, 2, 649. DOI
Keywords: O-H → O-SO2R • Mg-Alkyl+Silane • Si-Vinyl → Cu-Vinyl • Brook rearrangement • Cu-Vinyl+Enal • Zincke aldehyde • Pd-Deallylation • N-Allyl → N-H • Diels-Alder-inverse, EnAmine • Amine-5 • Hydrosilylation Alkyne • Mechanism • Mechanism • Mechanism • Knoevenagel condensation • ConjAdd M-OR • Ether-7 • N-H → N-Allyl •
Reagents: Hydroxide, sodium • Butadiene, 1-NR2 • KOtBu • Vinyl-SiR3 • RuCp(NCMe)3PF6 • HSiMe2(OEt) • Sulfonyl chloride, methane, NEt3 • Bromide, lithium • MeMgBr • Allyl-Br • Vinyl-SiR3 • Pd(PPh3)4 • NEtiPr2 • NaN(SiMe3)2 • CuBr • Malonate • Acetic anhydride • Acetate, sodium • Malonate •

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