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Total synthesis of (±)-δ-Araneosene:
Reference: Hu, T.; Corey, E. J. Org. Lett. 2002, 4, 2441. DOI
Keywords: Ketone enolate+Alkyl-X • Alkyl-X+Enolate • Alkyl-X → Alkyl-SO2R • Pd-enolate allylation • Tsuji-Trost allylation • McMurry coupling → Ene • CompE+-Allyl-Br/Carbonate+Enolate • Tsuji-Trost allylation • Pd-enolate allylation • Ozonolysis • CompOx-Alkene/Alkene+O3 • Ketone → Ketone-α-Halo • Ketone-α-S(O)nR → Ketone • Silyl ketone Brook • Mechanism •
Reagents: TASF • SiMe3-OTf • Sulfinate, benzene • Pd(PPh3)4 • Al(Hg) • O3 • Zn/Cu • SiMe3-OTf • NEtiPr2 • Carbonate, calcium • Pd2(dba)3 • Me2S • Acetate, potassium • Silyl ketone • Propenyl-Li • Allyl-Br •

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