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Total synthesis of Prostaglandin Fragment:
Reference: Corey, E. J.; Ensley, H. E. J. Am. Chem. Soc. 1975, 97, 6908. DOI
Keywords: Cu-Aryl+Enone • Enone+Cu-Aryl • ConjAdd Cu-R • Ketone epimerization • Ketone → Alkyl-OH • O-H → O-C(O)R • CarboxEster enolate oxidation • CarboxEster → CarboxEster-α-OR • Cyclopentadienide+Alkyl-X • Alkyl-X+Na-R • Diels-Alder, EnoateEster(asym) • Bicyclo(221) • CarboxEster → Alkyl-OH • Hydroperoxide → Alcohol • Baeyer-Villiger • Bicyclo(321) • Lactone-6 • Iodolactonization • Lactone-5 • Diol-1,2 cleavage •
Reagents: Aryl-MgX • CuCl • Hydroxide, potassium • Acryloyl-Cl • Chloromethyl ether • LiNiPr2 • P(OEt)3 • AlH4-Li+ • Cyclopentadienide • Chiral auxiliary-Ester • Acrylate • AlCl3 • O2 • Periodate, sodium • H2O2 • I2, KI • Bicarbonate, sodium •

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