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

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