Total synthesis of Ruguluvasines A and B:
| Reference: | Liras, S.; Lynch, C. L.; Fryer, A. M.; Vu, B. T.; Martin, S. F. J. Am. Chem. Soc 2001, 123, 5918. DOI |
| Reactions: | Pd/Sn-Aryl+Aryl-X • N-H → N-Me • Mannich • Alkyl-OH → Alkyl-CN • Nitrile → Imine • Lactone-5 • Mannich, vinylogous • Lactone-5 • Cyclohexane • Alkyl-X → Alkyl-CN • Cyanide+Alkyl-X • N-H → N-Boc • N-H → N-Cbz • N-Cbz → N-H • N-Boc → N-H • |
| Reagents: | CH2=NMe2+I- • Cyanide, potassium • Pd(PPh3)4 • Boc2O • Aryl-SnR3 • O=C(OBn)-Succinimide • MeI • Carbonate, cesium • H2, Pd • DMAP • Formaldehyde • DMF (solvent) • DMF (solvent) • AlHiBu2 • |