Total synthesis of 15-Deoxy-Prostaglandin E1:
| Reference: | Sih, C. J.; Salomon, R. G.; Price, P.; Peruzzoti, G.; Sood, R. Chem. Commun. 1972, 240 DOI |
| Reactions: | O-THP → O-H • ConjAdd Cu-Vinyl • Cu-Vinyl+Enone • CompE+-Ketone/CarboxEster+M-R • Li-Cyclopentadienide+Alkyl-X • Alkyl-X+Li-R • Singlet oxygen+Diene • O-H → O-THP • CarboxEster → CarboxAcid • Jones oxidation • Allyl-OH → Enone • |
| Reagents: | Cyclopentadienide • H2O2 • DHP • Vinyl-Li • CuI·PBu3 • Acetic acid • Baker's yeast • Al(OiPr)3 • CrO3, H2SO4 (Jones) • Hypochlorite, sodium • O2 (singlet) • |