Total synthesis of Jiadifenolide (Shenvi):
| Reference: | Lu H.; Martinez M. D.; Shenvi R. A. Nature Chem. 2014, 7, 604-607 DOI |
| Reactions: | Ketone → EnolSilane • Pauson-Khand • Lactone-5 • Knoevenagel condensation • Lactone-5 • Ozonolysis • CompOx-Alkene/Alkyne+O3 • ConjAdd Enolate • Aldehyde → Alkyne (-H2O) • KetoEster enolate+EnoateEster • KetoEster dianion+Alkyl-X • Cyclohexanone • Bicyclo(430) • Lactone → Lactone-α-Halo • CarboxEster enolate+Br2 • CompE+-Lactone/Lactone+Base • CarboxEster → CarboxEster-α-OR • Oxaziridine+Enolate • CarboxEster → CarboxEster-α-OR • Ketone → Alkyl-OH • CompRed-Ketone/Lactone+M-H • |
| Reagents: | Phosphazene base • O3 • SiO2 • LiNiPr2 • Mo(CO)6 • Bromide, R4N+ • LiNiPr2 • Ti(OiPr)4 • BH(OAc)3-Me4N+ • LiNiPr2 • CBr4 • Oxaziridine • NaSi(NMe2)3 • Sulphonyl fluoride, perfluorobutyl • Perbenzoic acid, 3-chloro • |