image

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) • CompNu-EnolEther/Enamide+Br2 • Ketone enamine+Ketone • Ketone → Enone • Radical coupling • Ketone → Imine •
Reagents: BH(Pinacol) • CBr4 • Vinyl-I • Periodate, sodium • Acetate, ammonium • Vinyl-B • Pd(PPh3)4 • Tl2CO3 • Vinyl-I • CuI • Carbonate, potassium • Fluoride, R4N+ • MnO2 • SiMe2tBu-OTf • NEt3 • Acrolein • Grubbs-Hoveyda • Methyl vinyl ketone • HSnBu3 • NEtiPr2 • HCl, H2O • BuLi(n) • Martin sulfurane • NBS • AIBN • HF·NEt3 • BH4-Na+ • Boc-Cl • IBX • SiMe3-I • AIBN •

Syntheses Home