Total synthesis of Warburganal (Goldsmith):
| Reference: | Goldsmith, D. J.; Kezar, H. S. Tetrahedron Lett. 1980, 21, 3543. DOI |
| Reactions: | Enal → Acetal • Claisen acylation, formate • Ketone enolate+Formate • KetoAldehyde → Enone • Aldehyde → Enal • Selenoxide-Ei → Enal • Li-Me+Ketone • Enone+Li-R • Dehydration → Diene • Alkene → Diol-1,2 • CompOx-Alkene/Alkene+OsO4 • Enal → Acetal • CompE+-Aldehyde/Ketone+glycol • |
| Reagents: | Formate, ethyl • SePh-Cl • Glycol • TsOH • Burgess reagent • OsO4 • Pyridine • H2O2 • Me-Li • |