Total synthesis of Ryanodol:
| Reference: | Chuang, K. V.; Xu, C.; Reisman, S. E. Science 2016, 353, 912. DOI |
| Reactions: | Enone → Enone-α-OR • Oxaziridine+Enolate • Enone enolate oxidation • Ketone → EnolTriflate • Mg-Alkynyl+Ketone • Ketone+Mg-Alkynyl • Cu-Vinyl+EnoateEster • EnoateEster+Cu-R • Mg-R → Cu-R • Pauson-Khand • Cyclopentenone • Bicyclo(430) • Bicyclo(330) • Enone → Enone-α-OR • Ketone → Ketone-1,2-di • Pd/Sn-Vinyl+Vinyl-X • Enone → Allyl-OH • CompRed-Ketone/CarboxEster+M-H • Hydrogenation Diene • O-BOM → O-H • Epoxidation, peracid • Radical cyclization(Alkyl) • Ynolether → EnoateEster • Lactone-6 • O-H → O-BOM • Ozonolysis • CompOx-Alkene/Alkyne+O3 • Mg-Alkynyl+Ketone • Ketone+Mg-Alkynyl • O-Bn → O-H • |
| Reagents: | Oxaziridine • KN(SiMe3)2 • Chloromethyl ether • Iodide, R4N+ • NEtiPr2 • Alkynyl-MgX • O3; PPh3 • Alkynyl-MgX • Vinyl-MgX • CuI • Rh(CO)2Cl • CO • SeO2 • NEtiPr2 • Vinyl-SnR3 • PdCl2(PPh3)2 • BH4-Li+ • H2, Pd • Peracetic acid, trifluoro • Li°/NH3 • |