image

Total synthesis of Isoamijiol, 14-deoxy:
Reference: Majetich, G.; Song, J. S.; Ringold, C.; Nemeth, G. A. Tetrahedron Lett. 1990, 31, 2239. DOI
Keywords: CarboxEster -> Alkyl-OH • Allyl-OH -> Allyl-Cl • Finkelstein reaction • Allyl-S(O)R -> Allyl-OH • Enone -> Alkene • Enone -> Allyl-OH • O-H -> O-SiMe2CH2Br • O-H -> O-SO2R • 2,3-Sigmatropic Sulfoxide • Radical cyclization(Alkyl) • Cu-Me+EnoateEster • ConjAdd-Elimination • C-Si -> C-OH, Alkyl • Selenoxide-Ei -> KetoEsterEnone • Ketoester -> Enone • Enone enolate+Alkyl-X • Allylic Oxidation -> Enone • Mg-Vinyl+Ketone • Enone-β-OR+Mg-R • Stork-Danheiser • Ketone -> Ketone-α-SeR • Ketone -> Vinyl-OP(O)(OR)2 • Cu-SiR3+Enone • ConjAdd Cu-SiR3 • Dehydration -> Ene • Alcohol inversion • Sakurai allylation • Si-Allyl+Enone • Enone+Si-R • ConjAdd Si-Allyl •
Reagents: NaH • H2O2 • Cu(SiMe2Ph)2Li • NaH • LiCuMe2 • AlH4-Li+ • MeLi • Vinyl-MgX • SPh-Cl • P(OMe)3 • AlCl3 • Hydroperoxide, tbutyl - Cr(CO)6 • AlH4-Li+ • SiMe2(CH2Br)-Cl • HSnBu3 • H2O2 • TsCl • Acetate, potassium • SePh-Cl • P(O)(OR)2Cl • AlEtCl2

Syntheses Home