Total synthesis of Fumagillol:
| Reference: | Boiteau, J.-G.; Van de Weghe, P.; Eustache, J. Org. Lett. 2001, 3, 2737. DOI |
| Reactions: | Selenide → Selenoxide • CarboxAmide(Evans) → CarboxAmide(Weinreb) • O-SiMe3 → O-H • O-PMB → O-H • CarboxAmide(Weinreb)+Mg-R • Mg-Vinyl+CarboxAmide • Selenoxide-Ei → Allyl-OR • Epoxidation, Ti • RCM → Enone • Cyclohexenone • Sulfonium ylide+Ketone • Epoxidation ylide • Corey-Chaykowsky • Hydrogenation Enone • CompRed-Enone/Alkene+H2 • Aldol-B-Evans • CarboxAmide enolate+Aldehyde (asym) • CarboxEster → Aldehyde • Selenolate+Lactone • O-H → O-PMB • Alkyl-X → Alkyl-SeR • O-H → O-SiMe3 • O-H → O-Me • |
| Reagents: | Periodate, R4N+ • NMe(OMe)-AlMe2 • SiMe3-Cl • Vinyl-MgX • RaNi • TsOH • MeI • Hydroperoxide, tbutyl - Ti • DDQ • Grubbs I • Chiral auxiliary (amide-Evans) • LiNiPr2 • Chiral auxiliary (amide-Evans) • Selenolate, phenyl • Diazomethane • PMBO-C(=NH)-CCl3 • AlHiBu2 • Sulfonic acid, Camphor • Me3SO+ I- • |