Total synthesis of Lysergic Acid:
| Reference: | Kornfeld, E. C.; Fornefeld, E. J.; Kline, G. B.; Mann, M. J.; Jones, R. G.; Woodward, R. B. J. Am. Chem. Soc. 1954, 76, 5256. DOI |
| Reactions: | CarboxAcid → CarboxCl • Friedel-Crafts Acylation • CarboxEster → CarboxCl • Cyclohexanone • Ketone → Ketone-α-Halo • N-H → N-C(O)R • Aldol-Na → Enone • Amine-6 • Bicyclo(440)-aza • N-H → N-Alkyl (2°) • Ketone-α-Halo → Ketone-α-NR2 • Allyl-OH → Allyl-Cl • Allyl-X → Allyl-CN • Nitrile → CarboxEster • Ketal → Ketone • N-C(O)R → N-H • Enone → Allyl-OH • CarboxEster → CarboxAcid • Indole synthesis • |
| Reagents: | SOCl2 • AlCl3 • Br2 • NaOMe • Acetyl chloride • BH4-Na+ • SOCl2 • HCN • HOMe (react) • Hydroxide, potassium • RaNi • |