Total synthesis of Hippadine:
| Reference: | Boger, D. L.; Wolkenberg, S. E. J. Org. Chem. 2000, 65, 9120-9124. DOI |
| Reactions: | N-Boc → N-H • Li/Br → Li-Aryl • Aldehyde → CarboxEster • Acetal → Aldehyde • Wittig-methoxymethyl • Diels-Alder, Intram, Yne • Tetrazine Cycloaddition • Retro-Diels-Alder → Arene • Amine-5 • Pyridazine synthesis • Diels-Alder, Intram, Ene • Pyridazine Cycloaddition • Retro-Diels-Alder → Arene • Lactam-6 • Benzene synthesis • Aryl-S(O)nR → Aryl-H • Dehydrogenation • Indole synthesis • Li-Aryl+CarboxAmide • CarboxAmide+Li-R • CarboxEster → CarboxAcid • CarboxAcid → CarboxAmide • |
| Reagents: | Aryl-Li • BuLi(n) • MnO2 • HOMe (react) • TsOH • PPh3=CH-OR • NEt3 • Boc2O • DMAP • HCl, H2O • Carbodiimide • Hydroxide, lithium • Butadiene, 1-NR2 • RaNi • DDQ • DMF (react) • HOBT • |