image

Total synthesis of Bilobalide (Crimmins):
Keywords: Li-R → Ce-R • Alkyl-OH → Ketone • O-SiMe2tBu → O-H • O-H → O-C(O)R (enol) • O-H → O-SiMe3 • Li-Alkyl+Aldehyde • Aldehyde+Li-R • Li-Nitrile+Aldehyde • Nitrile → Aldehyde • Aldol-Li → Aldol • Enone enolate+Aldehyde • Ketone → Ketone-α-OR • Ketone enolate oxidation • Ketone-α-OH cleavage • Aldehyde → Acetal • Baeyer-Villiger • Lactone-5 • Lactol → Lactone • Lactone-5 • Epoxidation, dioxirane • Diol-1,2 cleavage • Photochemistry 2+2 • Cyclobutane • Cyclopentane • CarboxEster → Alkyl-OH • Lactol → Lactone • Lactone-5 •
Reagents: BuLi(tert) • CeCl3 • DMSO, (COCl)2 (Swern) • LiCH2-CN • AlHiBu2 • Fluoride, potassium • Piv-Cl • SiMe3-Cl • MoOPH • Pb(OAc)4 • TsOH • AlH4-Li+ • Pb(OAc)4 • Perbenzoic acid, 3-chloro • CrO3, H2SO4 (Jones) • Dioxirane • CrO3, H2SO4 (Jones) •

Syntheses Home