Total synthesis of Aflatoxin M-1:
| Reference: | Buchi, G.; Weinreb, S. J. Am. Chem. Soc. 1969, 91, 5408-5409. DOI |
| Reactions: | O-H → O-C(O)R (phenol) • Ketone-α-Halo → Ketone-α-OR • Ketone+Mg-Alkyl • Mg-Allyl+Ketone • Alkene cleavage • Lemieux-Johnson oxidation • Aldehyde → Acetal • Acetate pyrolysis • O-H → O-Alkyl (phenol) • O-Me → O-H (phenol) • O-H → O-Bn (phenol) • Ketone → Ketone-α-Halo • O-C(O)R → O-H (phenol) • O-Bn → O-H (phenol) • |
| Reagents: | Sulfate, dimethyl • Carbonate, potassium • AlCl3 • Benzyl-X • Carbonate, potassium • Tribromide • Carbonate, calcium • Allyl-MgX • OsO4, NaIO4 • H2, Pd • Acetic anhydride • Flash vacuum pyrolysis • Bicarbonate, sodium • ZnCO3 • |