image

Total synthesis of Picrotoxinin:
Reference: Trost, B. M.; Krische, M. J. Am. Chem. Soc. 1996, 118, 233 DOI
Keywords: O-H -> O-SiMe2tBu • Mg-Alkynyl+Aldehyde • Felkin-Anh • O-H -> O-SiMe2tBu • Allyl-OH -> Allyl-Cl • Allyl-OH -> Enal • Pinnick oxidation • Enal -> EnoateAcid • Epoxidation, peracid • Alkene -> Diol-1,2 • Diol -> Ketal • O-H -> O-C(O)R • Ketal -> Diol • O-H -> O-SiMe3 • Lactone-5 • O-SiMe3 -> O-H • Enone enolate+Aldehyde • Aldol-Li -> Aldol • Li-Nitrile+Enone • Nitrile -> Aldehyde • Bromoetherification • Ether-5 • Allyl-X -> Allyl-OH • Reductive elimination - X/OR • Reductive elimination - OH/OH • Diol -> Alkene • Epoxidation, nucleophilic EnoateEster • Epoxide -> Diol • Lactone-5 • O-SiMe2tBu -> O-H • Pd-Alder-ene •
Reagents: LiNiPr2 • Formaldehyde • SiMe2tBu-Cl • LiCH2-CN • Tribromide, Pyridinium • AlHiBu2 • Bisulfate, sodium • Alkynyl-MgX • SiMe2tBu-Cl • SOCl2 • Carbonate, cesium • Carbonate, potassium • DMSO, (COCl)2 • Chlorite, sodium • Diazomethane • Peracetic acid, trifluoro • OsO4 • Zn° • Me2C(OMe)2 • Hydroxide, potassium • Diazomethane • Acetyl chloride • HCl, H2O • SiMe3-OTf • HF • DMF dimethylacetal • Hydroperoxide, tbutyl • LiN(SiMe3)2 • Cyanide, potassium • LiOtBu • Imidazole • Imidazole • Pd(OAc)2 • Fluoride, Bu4N+

Syntheses Home