Total synthesis of Gypsy Moth Sex Attractant:
| Reference: | Jacobson, M.; Beroza, M.; Jones, W. A. J. Am. Chem. Soc. 1961, 83, 4819-4824. DOI |
| Reactions: | O-THP → O-H • CompE+-CarboxEster/CarboxEster+H2O • Zn-Allenyl/Propargyl+Aldehyde • Aldehyde+Zn-R • Na-Alkynyl+Alkyl-X • Alkyl-X+Na-R • Na/H → Na-Alkynyl • Alkyl-X → Alkyl-CN • Nitrile → CarboxAcid • Alkyne → Ene-cis (Lindlar) • O-H → O-THP • CarboxAcid → Alkyl-OH • O-H → O-C(O)R • O-C(O)R → O-H • CompE+-CarboxEster/CarboxEster+H2O • |
| Reagents: | Propargyl-Br • Zn° • DHP • HCl • NH3 • Cyanide, sodium • Hydroxide, potassium • H2SO4 • H2, Pd • AlH4-Li+ • Acetyl chloride • Hydroxide, potassium • |