image

Total synthesis of Fumagillol:
Reference: Boiteau, J.-G.; Van de Weghe, P.; Eustache, J. Org. Lett.. 2001, 3, 2737. DOI
Keywords: 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 • Corey-Chaykowsky • Hydrogenation Enone • CompRed-Enone/Alkene+H2 • Aldol-B-Evans • CarboxEster → Aldehyde • Selenolate+Lactone • O-H → O-PMB • O-H → O-SiMe3 • O-H → O-Me •
Reagents: Periodate, R4N+ • NMe(OMe)-AlMe2 • SiMe3-Cl • Vinyl-MgX • RaNi • Me3SO+ I- • TsOH • MeI • Hydroperoxide, tbutyl • DDQ • Grubbs I • LiNiPr2 • Selenolate, phenyl • Diazomethane • Camphor sulfonic acid • AlHiBu2

Syntheses Home