Total synthesis of Cecropia Juvenile Hormone (Corey):
| Reference: | Corey, E. J.; Katzenellenbogen, J. A.; Gilman, N. W.; Roman, S. A.; Erickson, B. W. J. Am. Chem. Soc. 1968, 90, 5618. DOI |
| Reactions: | O-THP → O-H • Li/H → Li-Alkynyl • Birch reduction • Alkyl-X → Alkyl-H • Aldehyde → CH3 • Li-Alkynyl+Alkyl-X • Alkyl-X+Li-R • Cu-Me+Vinyl-X • Cu-Alkyl+Vinyl-X • Li-Allenyl/Propargyl+Alkyl-X • Allyl-X+Li-R • Si-Alkynyl → H-Alkynyl • Li-Alkynyl+Aldehyde • Aldehyde → CarboxEster • Alkyne → Vinyl-I • Al-Vinyl → I-Vinyl • Alkyne Hydroalumination • Alkyne Hydroalumination • Ozonolysis • CompOx-Alkene/Alkene+O3 • Aldehyde → Alkyl-OH • CompRed-Aldehyde/CarboxEster+M-H • Allyl-OH → Enal • Alkene → Bromohydrin • Bromohydrin → Epoxide • Epoxidation via halohydrin • O-H → O-SO2Ar • CarboxEster → Alkyl-OH • O-H → O-SO2Ar • Alkyl-OH → Alkyl-Br • Al-Vinyl → I-Vinyl • Alkyne → Vinyl-I • |
| Reagents: | Li°/NH3 • O3; Me2S • BH4-Na+ • TsCl, Py • AlH4-Li+ • TsCl, Py • Alkynyl-Li • Alkyl-Cuprate • PBr3 • Allenyl-Li • Alkynyl-SiR3 • AgNO3 • Cyanide, potassium • Alkynyl-Li • BuLi(n) • Formaldehyde • AlH4-Li+ • I2 • Me-Cuprate • MeI • MnO2 • Cyanide, sodium • MnO2 • HOMe (react) • AlH4-Li+ • NBS • |