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Total synthesis of Isoamijiol:
Reference: Majetich, G.; Song, J. S.; Ringold, C.; Nemeth, G. A. Tetrahedron Lett. 1990, 31, 2239. DOI
Keywords: CarboxEster → Alkyl-OH • Allyl-X → Allyl-Cl • O-H → O-SO2R • 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 • Si-Alkyl → HO-Alkyl • Selenoxide-Ei → KetoEsterEnone • Ketoester → Enone • Enone enolate+Alkyl-X • Alkyl-X+Enolate • Allylic Oxidation → Enone • Mg-Vinyl+Ketone • Enone-β-OR+Mg-R • Stork-Danheiser • Ketone → Ketone-α-SeR • Ketone → EnolPhosphate • Cu-SiR3+Enone • ConjAdd Cu-SiR3 • Dehydration → Ene • Alcohol inversion • Sakurai allylation • Si-Allyl+Enone • Enone+Si-R • ConjAdd Si-Allyl • Allylic oxidation → Allyl-OH •
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 • SeO2 • Hydroperoxide, tbutyl •

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