Total synthesis of Isoamijiol:
| Reference: | Majetich, G.; Song, J. S.; Ringold, C.; Nemeth, G. A. Tetrahedron Lett. 1990, 31, 2239. DOI |
| Reactions: | Allyl-S(O)R → Allyl-OH • Enone → Alkene • O-H → O-SiMe2CH2Br • O-H → O-SO2Ar • 2,3-Sigmatropic Sulfoxide • Radical cyclization(Alkyl) • Cu-Me+EnoateEster • ConjAdd-Elimination • ConjAdd Cu-Me • Si-Alkyl → HO-Alkyl • Selenoxide-Ei → KetoEsterEnone • KetoEster → Enone • Enone enolate+Alkyl-X • Allyl-X+Enolate • Allylic Oxidation → Enone • Mg-Vinyl+Ketone • Enone-β-OR+Mg-R • Stork-Danheiser • Ketone → Ketone-α-SeR • Cu-SiR3+Enone • ConjAdd Cu-SiR3 • Dehydration → Ene • Dehydrosulfonoxylation → Ene • Alkyl-OH inversion • Sakurai allylation • Si-Allyl+Enone • Enone+Si-R • ConjAdd Si-Allyl • Cycloheptane • Bicyclo(540) • Bicyclo(530) • Allylic oxidation → Allyl-OH • Enone → Allyl-OH • Ketone → EnolPhosphate • CarboxEster → Alkyl-OH • Allyl-OH → Allyl-Cl • Allyl-X → Allyl-Cl • O-H → O-SO2Me • Finkelstein reaction • |
| Reagents: | NaH • H2O2 • CuSiR3 • NaH • Me-Cuprate • AlH4-Li+ • Me-Li • Vinyl-MgX • SPh-Cl • P(OMe)3 • AlCl3 • Hydroperoxide, tbutyl - Cr • AlH4-Li+ • SiMe2(CH2Br)-Cl • HSnBu3 • H2O2 • TsCl • Acetate, potassium • SePh-Cl • P(O)(OR)2Cl • AlEtCl2 • SeO2 • Hydroperoxide, tbutyl • Sulfonyl chloride, methane • |