Total synthesis of Coniceine, δ- (Jung):
| Reference: | Jung, M. E.; Choi, Y. M. J. Org. Chem. 1991, 56, 6729. DOI |
| Reactions: | N-H → N-Alkyl • Amine-4 • N-H → N-C(O)R • Dehydrosulfonoxylation → EnAmine • Diels-Alder, Intram, Ene • Lactam-5 • Amine-6 • Bicyclo(430)-aza • Electrocyclic-4π • O-H → O-SO2Me • N-Bn → N-H • Hydrogenation alkene • Amine-6 • N-C(O)R → N-CH2R • |
| Reagents: | Epoxide • NH2CHPh2 • Sulfonyl chloride, methane, NEt3 • HCl • H2, Pd • NEt3 • KOtBu • H2, cat • AlH4-Li+ • Flash vacuum pyrolysis • |