Total synthesis of Majusculone:
| Reference: | Taber, D. F.; Sikkander, M. I.; Storck, P. H.. J. Org. Chem. 2007, 72, 4098 DOI |
| Reactions: | Dehydrohalogenation → Vinyl-X • Decarboxylation β-keto acid • Ozonolysis • Luche reduction • Enone enolate+Alkyl-X • Alkyl-X+Enolate • Carbene insertion • Spiro(54) • Aldol-Na → Enone • Cyclohexenone • Spiro(55) • Li-Me+Ketone • Ketone+Li-Alkyl • Dehydration → Ene • Allylic oxidation → Enone • Vinyl-H → Vinyl-Br • Ketal → Ketone • O-H → O-SO2Ar • ConjAdd Cu-Me • Cu-Me+Enone • CompE+-Enone/Vinyl-Br+Cu-R • Ketone → Ketal • Alkene → Dibromide-1,2 • Allyl-OH → Enone • |
| Reagents: | Br2 • Hydroxide, potassium • Vinyl-Br • Sulfonyl chloride, benzene • KOtBu • Hydroxide, lithium • Me-Cuprate • Hydrobenzoin • TsOH • KN(SiMe3)2 • O3 • Hydroxide, sodium • BH4-Na+, CeCl3 • HCl, MeOH • Me-Li • Dess-Martin • SOCl2 • CrO3 • Chiral auxiliary (ketal) • Hagemann's ester • CuBr • |