Total synthesis of Camptothecin (Rapoport):
| Reference: | Tang, C.; Rapoport, H. J. Am. Chem. Soc. 1972, 94, 8615. DOI |
| Reactions: | Hofmann elim → Enoate • Allylic oxidation → Allyl-OH • Claisen-Johnson • Mechanism • Friedlander • Lactone-6 • Lactone → Lactone-α-OR • Ketone → Alkyl-OH • O-C(O)OR → O-H • Alkyl-OH → Ketone • Quinoline synthesis • Allylic oxidation → Allyl-OH • |
| Reagents: | BH4-Na+ • Acetic anhydride • SeO2 • Acetic acid • Carbonate, potassium • Orthoester • Carbodiimide • SeO2 • H2SO4 • CuCl • DMF (solvent) • O2 • |