Total synthesis of Roseophilin:
| Reference: | Harrington, P. E.; Tius, M. A. J. Am. Chem. Soc. 2001, 123, 8509-8514. DOI |
| Reactions: | Imine → Aldehyde • Peterson → Enal • Knorr • Pyrrole synthesis • Bicyclo(330)-aza • N-SEM → N-H • N-SiR3 → N-H • Aldehyde azaenolate+Silyl-Cl • RCM → Ring-C • Cyclotridecane • Ce-Aryl+Ketone • Ketone+Li-Aryl • Hydrogenation alkene • CompRed-Alkene/Enone+H2 • Li-R → Ce-R • Li-Allenyl/Propargyl+CarboxAmide • CarboxAmide+Li-R • Allene synthesis • CarboxAcid → CarboxAmide • Appel • Nazarov • Cyclopentenone • Stetter • Aldehyde → Imine • Aldehyde azaenolate+Aldehyde • Pinnick oxidation • Aldehyde → CarboxAcid • N-H → N-SEM • Dehydration → EnAmine • Ketone → EnolCarboxylate • |
| Reagents: | LiNiPr2 • LiNiPr2 • Oxalic acid • Chlorite, sodium • PPh3, CBr4 • Chiral auxiliary (alcohol) • H2, Pd • Acetate, ammonium • KH • Furyl-Li • Fluoride, R4N+ • HCl, H2O • Grubbs I • CeCl3 • SiMe3-Cl • DMF (solvent) • HCl • NEt3 • Thiazolium • DMAP • Ti(OiPr)4 • SEM-Cl • Hexafluoroisopropanol (solvent) • Morpholine • |