Total synthesis of Dichroanone:
| Reference: | McFadden, R. M.; Stoltz, B. M. J. Am. Chem. Soc. 2006, 128, 7738 DOI |
| Reactions: | Wacker oxidation • Alkene → Ketone • Aldol-K → Enone • Robinson annulation, ketone • Cyclohexenone • Bicyclo(430) • Aldol-K → Enone • Cyclopentenone • Bicyclo(430) • Enone enolate+Enone • ConjAdd Enolate • Enone → EnolTriflate • Pd/Mg-Vinyl+Aryl-X • Friedel-Crafts Acylation • Baeyer-Villiger → Phenol • Phenol → Quinone • Quinone synthesis • Pd-enolate allylation (asym) • Tsuji-Trost allylation • Ketone enolate+Chlorocarbonate • Ketone → EnolCarbonate • Benzene synthesis • Quinone synthesis • Alkene isomerization • |
| Reagents: | LiN(SiMe3)2 • O=C(OAllyl)Cl (Alloc) • Pd2(dba)3 • Chiral catalyst (phosphine) • PdCl2 • Cu(OAc)2 • O2 • Hydroxide, potassium • LiN(SiMe3)2 • Hydroxide, potassium • LiNiPr2 • Tf2NPh • Propenyl-MgX • Pd(PPh3)4 • HCl, H2O • Cl2CH-OMe • TiCl4 • H2O2 • H2SO4 • IBX • Thiol, pentafluorophenyl • O2 • Hydroxide, sodium • PHOX • Methyl vinyl ketone • |