Total synthesis of Codling Moth Compound:
| Reference: | Marfat, A.; McGuirk, P. R.; Helquist, P. J. Org. Chem., 1979, 44, 1345; DOI 3888. DOI |
| Reactions: | Alkyl-X → Alkyl-I • Finkelstein reaction • Cu-Vinyl+CO2 • Carbocupration Alkyne • Cu-Alkyl+Alkyne • Mg-R → Cu-R • Alkyl-X → Alkyl-I • Cu-Vinyl+Epoxide • Epoxide+Cu-R • Carbocupration Alkyne • Cu-Alkyl+Alkyne • Mg-R → Cu-R • CarboxAcid → Alkyl-OH • O-H → O-SO2Ar • |
| Reagents: | TsCl, Py • Iodide, sodium • Alkyl-MgX • CuBr·SMe2 • Vinyl-Cu • CO2 • AlH4-Li+ • Alkyl-MgX • CuBr·SMe2 • Propyne • Alkynyl-Li • Vinyl-Cu • Epoxide • Chloride, ammonium • |