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Total synthesis of Isolongifolene New:
Reference: Piers, E.; Zbozny, M. Can. J. Chem., 1979, 57, 2249. DOI
Keywords: Allylic oxidation -> Enone • O-H -> O-C(O)R • Decarboxylation Krapcho • Enone -> Ketal • O-C(O)R -> O-H • O-H -> O-SO2R • Ketone -> Enone • Enone -> Dienone • Ketone -> Ketone-α-Halo • Enone enolate+Alkyl-X • Deconjugative alkylation • Hydroboration Alkene • Enone enolate+Alkyl-X • ConjAdd Cu-R • Cu-Me+Enone • ConjAdd Cu-R • Cu-Me+Enone • Ketone-α-Halo -> Enone • Enone -> Dienone •
Reagents: Photochemistry • NBS • Carbonate, calcium • KOtBu • BH(Siam)2 • H2O2, NaOH • Acetic anhydride, Py • Bromide, lithium • Glycol • AlH4-Li+ • TsCl, Py • KOtBu • DDQ • LiCuMe2 • Tribromide, ammonium • Carbonate, lithium • LiCuMe2

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