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

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