Total synthesis of Welwitindolinone A Isonitrile:
| Reference: | Reisman, S. E.; Ready, J. M.; Hasuoka, A.; Smith, C. J.; Wood, J. L. J. Am. Chem. Soc. 2006, 128, 1448-1449. DOI |
| Reactions: | Protecting group - Amine • O-H → O-C(O)NR2 • Alkene chlorination • Ketene Cycloaddition • Cyclobutane • Bicyclo(420) • CarboxCl → Ketene • Ketene synthesis • ConjReduct-Triflation • Enone ConjReduct • EnolTriflate → EnoateEster • Pd-Carboxylation • Semipinacol • Reductive amination, B-H • N-OR → N-H • Isocyanate+Li-R • Li-Allyl+Isocyanate • Li/H → Li-Allyl • Mg-Aryl+Ketone • Dehydration → Ene • Dehydroacetoxylation → Enone • Amine → Isocyanate • N-N=NR → N-H • Diol-1,2 → Ketone-α-OR • Acetal → Diol-1,2 • Ce-Alkyl+CarboxEster • CarboxEster+Mg-R • O-SiiPr3 → O-H • Ketone → Alkyl-OH • N-H → N-C(O)H • N-Boc → N-H • N-C(O)H → N=C • N-H → N-C(O)OR • O-H → O-C(O)NR2 • Ketone → Oxime • N-H → N-Boc • Diol-1,2 → Stannadioxolane • O-H → O-SiiPr3 • Alkyl-OH → Ketone • |
| Reagents: | Ketene • NEt3 • Aryl-MgX • RaNi • O=C(OR)Cl • Bicarbonate, sodium • Acetic acid • SnBu2(O) • NBS • SiiPr3-OTf • Lutidine • BH(sBu3)-Li+ • Tf2NPh • Pd2(dba)3 • CO • HOMe (react) • Me-MgBr • CeCl3 • Hypochlorite, sodium • CeCl3 • H2SiF6 • BH(OAc)3-Me4N+ • Martin sulfurane • Dess-Martin • Boc2O • DBU • NH2OMe • BH3CN-Na+ • Formic acetic anhydride • SmI2 • Formic acid • NEt3 • LiN(SiMe3)2 • DMAP • |