Total synthesis of Camptothecin (Danishefsky):
| Reference: | Volkmann, R.; Danishefsky, S.; Eggler, J.; Solomon, D. M. J. Am. Chem. Soc. 1971, 93, 5576–5577. DOI |
| Reactions: | Acetal → Aldehyde • CarboxAcid → CarboxEster • Dieckmann • CarboxEster enolate+CarboxEster • Cyclopentanone • Friedlander • Quinoline synthesis • ConjAdd Amine • ConjAdd EnAmine • Lactam-6 • Pyridine synthesis • Decarboxylation β-keto acid • CarboxEster enolate+Alkyl-X • Alkyl-X+Enolate • EnAmine+Aldehyde • Lactone-6 • CarboxEster → CarboxEster-α-OR • Decarboxylation β-keto acid • Aldehyde → CarboxAcid • |
| Reagents: | Acetylene dicarboxylate • Allene dicarboxylate • NEt3 • HCl, H2O • CrO3, H2SO4 (Jones) • HCl, MeOH • NaOMe • HCl, H2O • Hydroxide, sodium • CuO • NaH • Formaldehyde • H2SO4 • DMSO (solvent) • H2O2, KOtBu • HOMe (react) • |