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Total synthesis of Terpestacin:
Reference: Chan, J.; Jamison, T. F. J. Am. Chem. Soc. 2003, 125, 11514. DOI
Keywords: Ketone → Alkyl-OH • O-H → O-SiMe3 • O-SiiPr3 → O-H • ConjAdd Cu-R • Cu-Alkyl+Enone • Enone-α-Si+Cu-R • Alkyne isomerization • Li/I → Li-Alkyl • Pauson-Khand • Ketone → Ketone-α-OR • Ketone enolate+(Ox) • Ni-Aldehyde Hydrocarbation • Ketone enolate+Me-I • Ketone enolate+Alkyl-X, intram • Alkyl-X+Enolate • O-H → O-SiiPr3 • O-SiMe2tBu → O-H • Alkyl-OH → Ketone-α-OR • Allyl-OH → Allyl-I •
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 • PPh3, I2 • Imidazole •

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