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Total synthesis of Galbulimima Alkaloid 13:
Reference: Movassaghi, M.; Hunt, D. K.; Tjandra, M. J. Am. Chem. Soc. 2006, 128, 8126 DOI
Keywords: Corey-Fuchs • O-SiMe2tBu -> O-H • Allyl-OH -> Enone • N-Boc -> N-H • Enolsilane -> Enolsilane-α-Br • Imine -> Amine • N-H -> N-Boc • N-Boc -> N-H • Pd/B-Vinyl+Vinyl-X • Suzuki coupling • Hydroboration Alkyne • N-H -> N-Vinyl • Vinyl-Br -> Vinyl-N • Ketone -> Enolsilane • Olefin cross metathesis • Diels-Alder, Intram • Ketone azaenolate+Aldehyde • Dehydration -> Ene • Radical cyclization(Vinyl) • Ketone enamine+Ketone • Ketone -> Enone • Radical coupling • Ketone -> Imine •
Reagents: BH(Pinacol) • PPh3, CBr4 • Vinyl-I • Periodate, sodium • Acetate, ammonium • Vinyl-B • Pd(PPh3)4 • Tl2CO3 • Vinyl-I • CuI • Carbonate, potassium • Fluoride, Bu4N+ • MnO2 • SiMe2tBu-OTf • NEt3 • Acrolein • Grubbs-Hoveyda • Methyl vinyl ketone • AIBN • NEtiPr2 • HCl, H2O • BuLi(n) • Martin sulfurane • NBS • AIBN • HF·NEt3 • BH4-Na+ • Boc-Cl • IBX • SiMe3-I •

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