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Total synthesis of Graveolide:
Reference: Majetich, G.; Song, J. S.; Leigh, A. J.; Condon, S. M. J. Org. Chem. 1993, 58, 1030. DOI
Keywords: Ketal -> Enone • Allyl-OH -> Enone • Ketone -> Alkyl-OH • Lactone-5 • O-H -> O-SO2R • Alkyl-OH -> Ketone • Ketone -> Ketone-α-SeR • Prins • Cu-Vinyl+Allyl-X • Si-Allyl+Enone • ConjAdd Si-Allyl • Sakurai allylation • Selenoxide-Ei -> Enone-5 • Ketone -> Enone • Li/Br -> Li-Vinyl • Hydroboration Alkene • Li-Vinyl+Enone • Lactone enolate+Formaldehyde • ConjReduct-Alkylation Enone • Ketone enolate+Me-I • Mechanism • RC-Alkyl-OH/Alkyl-OH+O2/Pt •
Reagents: BuLi(n) • CuSPh • Vinyl-Cu • Allyl-I • Allyl-SiR3 • Propenyl-Li • Cr2O7·2PyH (PDC) • Allyl-SiR3 • AlEtCl2 • Formaldehyde • AlMe2-Cl • Li°/NH3 • MeI • BH3 • O2, PtO2 • BH4-Na+ • LiNiPr2 • TsCl, Py • DBU • CrO3Cl·PyH (PCC) • SePh-Cl • Periodate, sodium • H2O2, NaOH • Formaldehyde •

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