Total synthesis of Frullanolide:
| Reference: | Still, W. C.; Schneider, M. J. J. Am. Chem. Soc. 1977, 99, 948. DOI |
| Reactions: | Wharton transposition • Enone epoxidation, nucleophilic • Iodolactonization • Lactone-5 • Dehydrohalogenation → Ene • Hofmann elim → Enoate • ConjAdd Amine • CarboxEster → Ketene acetal • Claisen-Ireland • Mechanism • Ketone → Hydrazone • CarboxAcid → CarboxEster • Mechanism • Furst-Plattner diaxial • |
| Reagents: | H2O2, NaOH • Hydrazine • BuLi(n) • Acryloyl-Cl • Pyrrolidine • Carbonate, potassium • Hydroxide, potassium • I2, KI • DBU • LiNiPr2 • SiEt3-Cl • |