Total synthesis of Cerulenin (Boeckman) New:
| Reference: | Boeckman, R. K. Jr.; Thomas, E. W. J. Am. Chem. Soc. 1977, 99, 2805-2806, DOI; J. Am. Chem. Soc. 1979, 101, 987-994s://dx.doi.org/10.1021/ja00450a071" target = "_blank" rel="noopener"rget = "_blank" rel="noopener">DOI |
| Reactions: | Mg/H → Mg-Alkynyl • Mg-R → Cu-R • Cu-Alkynyl+Alkyl-X • O-THP → O-H • Alkyne → Ene-trans • Alkyl-OH → Aldehyde • Li-Alkynyl+Aldehyde • Aldehyde+Li-R • Alkyne → Ene-cis (Lindlar) • Epoxidation, V • CompOx-Alkene/Alkene+M-OOR • Alkyl-OH → CarboxAcid • Lactone-5 • CompOx-Alkyl-OH/Alkyl-OH+AgCO3 • Lactone → CarboxAmide • Alkyl-OH → Ketone • |
| Reagents: | Alkyl-MgBr • CuCl • Propargyl-Br • HCl, H2O • Li°/NH3 • CrO3Cl·PyH (PCC) • Alkynyl-Li • H2, Pd • Hydroperoxide, tbutyl - V • NH3 • CrO3Cl·PyH (PCC) • |