Total synthesis of Aspidospermidine:
| Reference: | Sharp, L. A.; Zard, S. Z. Org. Lett. 2006, 8, 831-834. DOI |
| Reactions: | Friedel-Crafts Acylation • Lactone-5 • Birch alkylation • CarboxEster enolate+Alkyl-X • Bromoacetate+Enolate • Fischer Indole • Indole synthesis • Hydrogenolysis Ketone • Ketone → CH2 • N-C(O)R → N-CH2R • CompRed-CarboxAmide/Ketone+M-H • CompRed-CarboxAmide/CarboxEster+M-H • Bicyclo(430)-aza • EnoateEster enolate+Alkyl-X • Bromoacetate+Enolate • Decarboxylation Krapcho • Lactam-5 • Mechanism • Radical cyclization(Aminyl) • Amine-6 • Lactam-5 • Bicyclo(440)-aza • CarboxAcid → CarboxAmide • O-H → O-C(O)R • O-H → O-Alkyl (phenol) • |
| Reagents: | Acetyl chloride • H2, Pd • Carbonate, potassium • Li°/NH3 • HCl, H2O • O=C(OtBu)Cl (Boc) • Benzoyl chloride • BH-BBN • Chloride, lithium • Hydrazine, phenyl • BH4-Na+ • Bromoacetate • DMF (solvent) • HSnBu3 • |