Total synthesis of Erogorgiaene:
| Reference: | Cesati, III, R. R.; de Armas, J.; Hoveyda, A. H. J. Am. Chem. Soc 2004, 126, 96. DOI |
| Reactions: | Pd-Heck coupling • Cu-Me+Enone • ConjAdd Cu-R (asym) • Zn-R → Cu-R • Pd/Sn-Alkynyl+Aryl-X • Enyne metathesis • Cyclohexene • EnolTriflate → Vinyl-H • Si-Alkynyl → H-Alkynyl • Ketone → EnolTriflate • Ketone → EnolSilane • EnolSilane → Ketone enolate • Ketone → Alkyl-OH • Alkyl-OH → Ketone • Olefin cross metathesis • Cu-Me+Enone • ConjAdd Cu-R (asym) • Zn-R → Cu-R • Alkyl-OH → Alkyl-I • Cu-Vinyl+Alkyl-X • Alkyl-X+Cu-R • Mg-R → Cu-R • Ozonolysis • CarboxAcid → Alkyl-OH • Ketone → EnolSilane • |
| Reagents: | Methyl vinyl ketone • Pd(OAc)2 • Chiral catalyst (phosphine) • ZnMe2 • Cu(OTf)2 • Alkynyl-SnR3 • Pd(PPh3)4 • BHT • LiTMP • SiMe3-Cl • Me-Li • Tf2NPh • HSnBu3 • Pd(PPh3)4 • Carbonate, potassium • Grubbs-Hoveyda • Methyl vinyl ketone • Chiral catalyst (phosphine) • ZnMe2 • Cu(OTf)2 • BH4-Na+ • Li°/NH3 • Dess-Martin • LiNiPr2 • O3; Me2S • AlH4-Li+ • I2 • Vinyl-MgX • CuI • SiMe3-Cl • |