Total synthesis of Coccolinine New:
| Reference: | Sano, T.; Toda, J.; Maehera, M. Can. J. Chem. 1987, 65, 94-98. DOI |
| Reactions: | N-H → N-C(O)R • Bischler-Napieralski • Amine-6 • EnAmine acylation • Lactam-6 • N-H → N-C(O)R • Diels-Alder, EnoateEster • Spiro(55)-aza • Bicyclo(430)-aza • O-H → OSO2Me • Ketone → Alkyl-OH • EnolSilane → Ketone • Dehydration → Enone • Decarboxylative elimination • Enone → Allyl-OH • Meerwein-Ponndorf-Verley reduction • O-H → O-Me • CarboxAmide → Amine • |
| Reagents: | Carbonate, potassium • Butadiene, 2-OR • Butadiene, 1-OR • BH4-Li+ • HCl, H2O • Sulfonyl chloride, methane, Py • MgCl2 • Al(OiPr)3 • MeI • Hydroxide, potassium • AlH3 • AlCl3 • Danishefsky diene • |