Total synthesis of Cecropia Juvenile Hormone (Van Tamelen):
| Reference: | Van Tamelen, E. E.; McCormick, J. P. J. Am. Chem. Soc. 1970, 92, 737–738. DOI |
| Reactions: | Epoxidation, peracid • CompOx-Alkene/Alkene+Peracid • Epoxide → Allyl-OH • Allyl-OH → Enal • Enal → EnoateEster • Cu-Me+Allyl-X • Allyl-X+Cu-R • O-H → O-CPh3 • CompNu-O-H/O-H+R-X • O-H → O-SO2Ar • O-CPh3 → O-H • Alkene → Bromohydrin • CompOx-Alkene/Alkene+Br2 • Bromohydrin → Epoxide • Epoxidation via halohydrin • O-H → O-C(O)R • |
| Reagents: | Perbenzoic acid, 3-chloro • Carbonate, potassium • LiNEt2 • TsCl, Py • Chloride, lithium • HCl, THF • MnO2 • MnO2 • HOMe (react) • NBS • Me-Cuprate • Ph3CCl • |