Total synthesis of Prostaglandin-PGF1α:
| Reference: | Marino, J. P.; Pradilla, R. F.; Laborde, E. J. Org. Chem. 1987, 52, 4898. DOI |
| Reactions: | O-SiMe2tBu → O-H • O-SiMe2tBu → O-H • Epoxidation, V • Cu-Vinyl+Epoxide • Epoxide+Cu-R • Ketone → EnolSilane • Cu-Alkyl+Epoxide • Epoxide+Cu-R • Alkyl-OH → CarboxAcid • CompOx-Alkyl-OH/Alkyl-OH+O2/Pt • Alkyl-OH → CarboxAcid • CompOx-Alkyl-OH/Alkyl-OH+O2/Pt • Alkyl-OH → Ketone-α-OR • Ketone → EnolSilane • |
| Reagents: | Epoxide • Vinyl-Cu • Hydroperoxide, tbutyl • CrO3·Py2 (Collins) • LiNiPr2 • BH(sBu3)-Li+ • HF • O2, PtO2 • HF • O2, PtO2 • HF • SiEt3-Cl • Alkyl-Cu • |