image

Total synthesis of Hippadine:
Reference: Boger, D. L.; Wolkenberg, S. E. J. Org. Chem. 2000, 65, 9120-9124. DOI
Keywords: Li-Aryl+CarboxAmide • CarboxAmide+Li-R • N-Boc → N-H • CarboxAcid → CarboxAmide • CarboxEster → CarboxAcid • Li/Br → Li-Aryl • Aldehyde → CarboxEster • Acetal → Aldehyde • Wittig-methoxymethyl • Diels-Alder, Intram • Diels-Alder, Yne • Retro-Diels-Alder → Arene • Diels-Alder, Intram • Retro-Diels-Alder → Arene • Aryl-S(O)nR → Aryl-H • Dehydrogenation •
Reagents: BuLi(n) • DMF (react) • MnO2 • TsOH • PPh3=CH-OMe • NEt3 • Boc2O • DMAP • HCl, H2O • Carbodiimide • Hydroxide, lithium • RaNi • DDQ •

Syntheses Home