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Total synthesis of Cecropia Juvenile Hormone:
Reference: Corey, E. J.; Katzenellenbogen, J. A.; Gilman, N. W.; Roman, S. A.; Erickson, B. W. J. Am. Chem. Soc. 1968, 90, 5618. DOI
Keywords: Ozonolysis • CompOx-Alkene/Alkene+O3 • Aldehyde → Alkyl-OH • O-H → O-SO2R • CarboxEster → Alkyl-OH • O-H → O-SO2R • Alkyl-OH → Alkyl-Br • Alkyne → Vinyl-I • Al-Vinyl → I-Vinyl • Allyl-OH → Enal • Alkene → Bromohydrin • Bromohydrin → Epoxide • Birch reduction • Alkyl-X → Alkyl-H • Li-Alkynyl+Alkyl-X • Alkyl-X+Li-R • Cu-Alkyl+Vinyl-X • Cu-Alkyl+Vinyl-X • Li-Allenyl/Propargyl+Alkyl-X • Alkyl-X+Li-R • Si-Alkynyl → H-Alkynyl • Li-Alkynyl+Aldehyde • Aldehyde+Li-R • Aldehyde → CarboxEster • Alkyne → Vinyl-I • Al-Vinyl → I-Vinyl • Alkyne Hydroalumination • Alkyne Hydroalumination •
Reagents: Li° • O3 • Me2S • BH4-Na+ • TsCl, Py • AlH4-Li+ • TsCl, Py • Allenyl-Li • LiCuEt2 • PBr3 • Allenyl-Li • AgNO3 • Cyanide, potassium • BuLi(n) • Formaldehyde • AlH4-Li+ • I2 • LiCuMe2 • MeI • MnO2 • Cyanide, sodium • MnO2 • NBS • AlH4-Li+ • I2

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