Total synthesis of Galbulimima Alkaloid 13 (Movassaghi):
| Reference: | Movassaghi, M.; Hunt, D. K.; Tjandra, M. J. Am. Chem. Soc. 2006, 128, 8126 DOI |
| Reactions: | Hydroboration Alkyne • BoronateEster → BoronicAcid • N-Boc → N-H • Radical coupling • Ketone → Imine • Amine-5 • Pd/B-Vinyl+Vinyl-X • Corey-Fuchs • N-H → N-Vinyl • Vinyl-Br → Vinyl-N • Ketone → EnolSilane • O-SiMe2tBu → O-H • Allyl-OH → Enone • Olefin cross metathesis • Diels-Alder, Intram, Ene • Bicyclo(440) • Ketone azaenolate+Aldehyde • Imine → Amine • Dehydration → Ene • Radical cyclization(Vinyl) • CompNu-EnolEther/Enamide+Br2 • Cyclopentene • Ketone enamine+Ketone • Bicyclo(321) • EnolSilane → EnolSilane-α-Br • Ketone → Enone • N-H → N-Boc • N-Boc → N-H • |
| Reagents: | BH(Pinacol) • Periodate, sodium • Acetate, ammonium • Vinyl-BR2 • Methyl vinyl ketone • HSnBu3 • NEtiPr2 • HCl, H2O • BuLi(n) • AIBN • Pd(PPh3)4 • Tl2CO3 • Vinyl-I • Vinyl-BR2 • CuI • Carbonate, potassium • Fluoride, R4N+ • MnO2 • SiMe2tBu-OTf • NEt3 • Acrolein • Grubbs-Hoveyda • Martin sulfurane • NBS • HSnBu3 • HF·NEt3 • BH4-Na+ • AIBN • O=C(OtBu)Cl (Boc) • IBX • SiMe3-I • PPh3=CBr2 • PPh3, CBr4 • |