Total synthesis of δ-Araneosene:
| Reference: | Hu, T.; Corey, E. J. Org. Lett. 2002, 4, 2441. DOI |
| Reactions: | Ketone enolate+Alkyl-X • Allyl-X+Enolate • CompE+-Allyl-Br/Carbonate+Enolate • Pd-enolate allylation • Tsuji-Trost allylation • Cycloundecane • McMurry coupling → Ene • Cyclopentene • Bicyclo(930) • Tsuji-Trost allylation • Pd-enolate allylation • Ozonolysis • CompOx-Alkene/Alkene+O3 • Ketone → Ketone-α-Halo • EnolSilane → Ketone-α-Halo • Ketone-α-S(O)nR → Ketone • Silyl ketone Brook • Brook rearrangement • Alkyl-X → Alkyl-SO2R • Mechanism • |
| Reagents: | TASF • Allyl-Br • SiMe3-OTf • Sulfinate, benzene • Pd(PPh3)4 • Al(Hg) • O3; Me2S • Zn/Cu • SiMe3-OTf • NEtiPr2 • Carbonate, calcium • Pd2(dba)3 • Acetate, potassium • Silyl ketone • Propenyl-Li • Allyl-Br • Allyl-Li • |