Total synthesis of Aflatoxin B1:
| Reference: | Buchi, G; Foulkes, D. M.; Kurono, M.; Mitchell, G. F.; Schneider, R. S. J. Am. Chem. Soc. 1967, 89, 6745–6753. DOI |
| Reactions: | O-Bn → O-H (phenol) • Wittig-carboxymethyl → EnoateEster • Lactone-6 • Wittig (intram) • Allylic oxidation → Enal • Enal → Aldehyde • ConjReduct Enal • Ether-5 • Pechmann condensation • Friedel-Crafts Alkylation • Lactone-6 • Pyrone synthesis • Friedel-Crafts Acylation, Ene • Lactone-5 • Cyclopentenone • Lactone → Lactol • CompRed-Lactone/Ketone+M-H • Ester Pyrolysis • O-H → O-C(O)R (phenol) • CompNu-Phenol/Phenol+RC(O)X • O-H → O-Alkyl (phenol) • O-C(O)R → O-H (phenol) • CarboxAcid → CarboxCl • CarboxEster → CarboxAcid • O-H → O-Bn (phenol) • |
| Reagents: | Acetic anhydride • Diazomethane • HCl, MeOH • Benzyl-X • PPh3=CH-CO2R • SeO2 • Zn° • Acetic acid • Pd/C • HCl, MeOH • HCl • Oxalyl chloride • AlCl3 • BH(Siam)2 • Acetic anhydride • Carbonate, potassium • |