image

Total synthesis of Vernolepin:
Reference: Danishefsky, S.; Kitahara, T.; Schuda, P. F.; Etheredge, S. J. J. Am. Chem. Soc. 1976, 98, 3028. DOI
Keywords: CarboxEster -> CarboxAcid • Alkene cleavage • CarboxAcid -> CarboxEster • Lactone -> Orthoester • Lactone -> Lactol • Orthoester -> CarboxEster • Lactone-5 • Lactone-6 • O-H -> O-THP • CarboxEster enolate+Aldehyde • O-H -> O-SO2R • Dehydrosulfonoxylation -> EnoateEster • O-THP -> O-H • Iodolactonization • Furst-Plattner diaxial • Lactone-5 • Wittig-methyl • Epoxidation, peracid • Henbest • Dehydrohalogenation -> Allyl-OR • Diels-Alder, EnoateEster • Furst-Plattner diaxial • CarboxAcid enolate+Epoxide • Epoxide+Enolate •
Reagents: Hydroxide, sodium • I2, KI • DBU • Hydroxide, sodium • OsO4 • Pb(OAc)4 • Diazomethane • BHsBu3-Li+ • Amberlite • Glycol • AlHiBu2 • PPh3=CH2 • TsOH • DHP • LiNiPr2, HMPA • MeSO2Cl, NEt3 • DBU • Formaldehyde • Perbenzoic acid, 3-chloro • Acetic anhydride • Ba(ClO3)2 • Epoxide • CH2=C(OLi)2

Syntheses Home