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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.
Keywords: Ketal -> Enone --- Allyl-OH -> Enone --- Ketone -> Alkyl-OH --- Lactone-5 --- O-H -> O-SO2R --- Alkyl-OH -> Ketone --- Ketone -> α-Selenoketone --- Prins --- Cu-Vinyl+Allyl-X --- Si-Allyl+Enone --- ConjAdd Si-Allyl --- 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
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) --- PhSeCl --- Periodate, sodium --- H2O2, NaOH --- Formaldehyde

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