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Total synthesis of Prostaglandin-PGF:
Reference: Marino, J. P.; Pradilla, R. F.; Laborde, E. J. Org. Chem. 1987, 52, 4898. DOI
Keywords: Alkyl-OH → Ketone-α-OR • Ketone → EnolSilane • Alkyl-OH → CarboxAcid • O-SiMe2tBu → O-H • CompOx-Alkyl-OH/Alkyl-OH+O2/Pt • Epoxidation, V • Cu-Vinyl+Epoxide • Epoxide+Cu-R • Ketone → EnolSilane • Cu-Alkyl+Epoxide • Epoxide+Cu-R •
Reagents: Epoxide • Vinyl-Cu • Hydroperoxide, tbutyl - VO(acac)2 • CrO3·Py2 (Collins) • LiNiPr2 • BH(sBu3)-Li+ • HF • O2, PtO2 • HF • O2, PtO2 • HF • SiEt3-Cl • Alkyl-Cu •

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