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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 • Allyl-X+Cu-R • Selenoxide-Ei → Enone • Ketone → Enone • Li/Br → Li-Vinyl • Hydroboration alkene • Li-Vinyl+Ketone • Enone+Li-R • Lactone enolate+Aldehyde • ConjReduct-Alkylation • Ketone enolate+Me-I • Enone ConjReduct • CompOx-Alkyl-OH/Alkyl-OH+O2/Pt • Si-Allyl+Enone • Enone+Si-R • ConjAdd Si-Allyl • Sakurai allylation • Mechanism •
Reagents: BuLi(n) • CuSPh • Vinyl-Cu • Allyl-I • Allyl-SiR3 • Propenyl-Li • Cr2O7·2PyH (PDC) • 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 • Allyl-SiR3 • AlEtCl2

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