Total synthesis of Juvabione (Neier):
| Reference: | Soldermann, N.; Velker, J.; Vallet, O.; Stoeckli-Evans, H.; Neier, R. Helv. Chim. Acta 2000, 83, 2266. DOI |
| Reactions: | Arndt-Eistert • Diazoketone → Ketene • Fe/Mg-Alkyl+CarboxCl • CarboxCl+Mg-R • Alkene isomerization • Diazoketone • CarboxCl → Diazoketone • Diels-Alder, EnoateEster • Claisen-Ireland • Aldehyde → Enol-R • CarboxEster → Ketene acetal • CarboxAcid → CarboxCl • CarboxAcid → CarboxCl • |
| Reagents: | KOtBu • Butadiene, 1-OR • NaN(SiMe3)2 • SiMe2tBu-Cl • Oxalyl chloride • Diazoketone • Ag(OC(O)CF3)2 • DBU • Oxalyl chloride • Crotonaldehyde • Alkyl-MgX • Fe(acac)3 • DMPU (solvent) • Diazomethane • Acrylate • |