Total synthesis of Isopetasol (Yamakawa):
| Reference: | Yamakawa, K.; Izuta, I.; Oka, H.; Sakaguchi, R. Tetrahedron Lett. 1974, 2187. DOI |
| Reactions: | Ketone → Alkyl-OH • CompRed-Ketone/Enone+M-H • KetoEster+Li-Me • CompE+-CarboxEster/Ketone+M-R • Claisen acylation, carbonate • Ketone enolate+Carbonate • Robinson annulation, ketone • Ketone enolate+Enone • Cyclohexenone • Bicyclo(440) • Ketone → Ketal • CompE+-Ketone/Enone+glycol • Ketal → Ketone • Dehydration → Enoate • |
| Reagents: | Methyl vinyl ketone • TsOH • Glycol • O=C(OR)2 • NaH • Me-Li • BH4-Na+ • |