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Total synthesis of Terpestacin:
Reference: Chan, J.; Jamison, T. F. J. Am. Chem. Soc. 2003, 125, 11514. DOI
Keywords: O-H → O-SiMe3 • O-SiiPr3 → O-H • ConjAdd Cu-R • Cu-Alkyl+Enone • Enone-Cu-R • Alkyne isomerization • Li/I → Li-Alkyl • CompE+-Alkyl-I/Alkynyl-H+Li-R • Pauson-Khand • Cyclopentenone • Ketone → Ketone-α-OR • Ketone enolate oxidation • Ni-Aldehyde Hydrocarbation • Ketone enolate+Me-I • Ketone enolate+Alkyl-X (intram) • Alkyl-X+Enolate (intram) • CompE+-Si-O/Si-O+H2O • CompE+-Si-O/Si-O+H2O • O-SiMe3 → O-H • CompE+-Si-O/Si-O+H2O • O-SiMe2tBu → O-H • Ketone → Alkyl-OH • Alkyl-OH → Ketone-α-OR • Allyl-OH → Allyl-I • O-H → O-SiiPr3
Reagents: NMO • Alkyl-Li • BuLi(tert) • BH4-Na+ • Fluoride, R4N+ • KOtBu • SiMe3-Cl • Fluoride, R4N+ • KN(SiMe3)2 • Carbonate, potassium • CuI • O2 • P(OEt)3 • DMSO (solvent) • Ni(cod)2 • Chiral catalyst • MeI • LiN(SiMe3)2 • SiiPr3-OTf • Hydroxide, sodium • RuO4-Pr4N+, NMO • HCl, H2O • Imidazole • PPh3

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