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Total synthesis of Prostaglandin PGE1 Methyl Ester:
Reference: Arnold, L. A.; Naasz, R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc 2001, 123, 5841. DOI
Keywords: Allyl-OR isomerization • Cu-Alkyl+Enone • Enone+Cu-R • ConjAdd-aldol(asym) Cu-R • ConjAdd Cu-R • Aldol-Zn • Ketone → Alkyl-OH • Si-Vinyl → H-Vinyl • O-H → O-C(O)R • O-C(O)R → O-H • Ketal → Ketone •
Reagents: Zn(BH4)2 • Fluoride, R4N+ • Acetic anhydride, DMAP • PdCl2(MeCN)2 • Carbonate, potassium • DMSO (solvent) • Alkyl-ZnX • Cu(OTf)2 • Chiral catalyst •

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