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Total synthesis of Cecropia Juvenile Hormone New:
Reference: Corey, E. J.; Katzenellenbogen, J. A.; et al J. Am. Chem. Soc. 1968, 90, 5618. DOI
Keywords: Ozonolysis • Aldehyde -> Alkyl-OH • O-H -> O-SO2R • CarboxEster -> Alkyl-OH • O-H -> O-SO2R • Alkyl-OH -> Alkyl-Br • Alkyne Hydroalumination • Alkyne->Vinyl-I • Allyl-OH -> Enal • Alkene -> Bromohydrin • Bromohydrin • Birch reduction • Alkyl-OSO2R -> Alkyl-H • Li-Alkynyl+Alkyl-X • Cu-Alkyl+Vinyl-X • Cu-Alkyl+Vinyl-X • Li-Allenyl/Propargyl+Alkyl-X • Alkynyl-Si -> Alkynyl-H • Li-Alkynyl+Aldehyde • Aldehyde+Li-R • Aldehyde -> CarboxEster • Alkyne->Vinyl-I • Alkyne Hydroalumination •
Reagents: O3 • Me2S • BH4-Na+ • TsCl • AlH4-Li+ • TsCl • Alkynyl-Li • LiCuEt2 • PBr3 • AgNO3 • Cyanide, potassium • BuLi(n) • Formaldehyde • AlH4-Li+ • I2 • LiCuMe2 • MnO2 • Cyanide, sodium • MnO2 • NBS • AlH4-Li+ • I2

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