Total synthesis of Akuammicine:
| Reference: | Bonjoch, J.; Sole, D.; Garcia-Rubio, S.; Bosch, J. J. Am. Chem. Soc. 1997, 119, 7230. DOI |
| Reactions: | Si-Propargyl+Enone • Enone+Si-R • Amine-6 • Bicyclo(331)-aza • Allene synthesis • Ketone → EnolSilane • EnolSilane → Ketone-α-SeR • Reductive amination, B-H • Amine-5 • Bicyclo(430)-aza • Selenoxide-Ei → Enone • Ketone → Enone • Claisen acylation, Mander • Ketone enolate+Mander • Mander+enolate • N-H → N-Propargyl • Nitro → Amine • Indole synthesis • CompRed-Nitro/Alkene+H2 • Hydrogenation Allene • CompRed-Allene/Enoate+H2 • Ozonolysis • N-Me → N-C(O)OR • Ketone → Ketone-α-SeR • N-C(O)OR → N-H • KetoEster → EnAmine • |
| Reagents: | Propargyl-Si • BF3·OEt2 • LiNiPr2 • H2, Pd • O3 • NH2Me • NH(SiMe3)2 (HMDS) • SiMe3-I • SePh-Cl • O3 • Propargyl-I • Propargyl-Si • Carbonate, potassium • HCl • H2, Pd • O=C(OR)CN • NHiPr2 • BH3CN-Na+ • O=C(OR)Cl • |