Total synthesis of Patulolide B:
| Reference: | Ronsheim, M. D.; Zercher, C. K. J. Org. Chem. 2003, 68, 1878. DOI |
| Reactions: | KetoEster dianion+Alkyl-X • Allyl-X+Enolate • RCM → Lactone • Lactone-9+ • Cu-Allyl+Epoxide • Epoxide+Cu-R • Mg-R → Cu-R • Dehydrohalogenation → Enone • Ketone-α-Halo → Enone • Hydrogenation alkene • Carbene insertion • O-H → O-C(O)R • |
| Reagents: | Epoxide • CuI • NaH • BuLi(n) • Allyl-Br • H2, Pd • DBU • DBU • Allyl-MgX • Ketene dimer • CH2I2, ZnEt2 • I2 • Grubbs I • |