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

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