Total synthesis of Vernolepin:
| Reference: | Danishefsky, S.; Kitahara, T.; Schuda, P. F.; Etheredge, S. J. J. Am. Chem. Soc. 1976, 98, 3028. DOI |
| Reactions: | O-THP → O-H • Iodolactonization • Furst-Plattner diaxial • Lactone-5 • Wittig-methyl • Epoxidation, peracid • CompOx-Alkene/Enone+Peracid • Dehydrohalogenation → Allyl-OR • Diels-Alder, EnoateEster • Bicyclo(440) • Furst-Plattner diaxial • CarboxAcid enolate+Epoxide • Epoxide+Enolate • Aldehyde → Alkyl-OH • CompRed-Aldehyde/CarboxEster+M-H • CarboxEster enolate+Aldehyde • CarboxEster → CarboxAcid • Alkene cleavage • Criegee oxidation • CarboxAcid → CarboxEster • Henbest • Lactone → Orthoester • Lactone → Lactol • Orthoester → CarboxEster • Lactone-5 • Lactone-6 • O-H → O-SO2Me • Dehydrosulfonoxylation → EnoateEster • O-H → O-THP • Lactone-6 • |
| Reagents: | Hydroxide, sodium • I2, KI • DBU • Hydroxide, sodium • OsO4 • Pb(OAc)4 • Diazomethane • BH(sBu3)-Li+ • Amberlite • Glycol • AlHiBu2 • PPh3=CH2 • TsOH • LiNiPr2 • Sulfonyl chloride, methane, NEt3 • DBU • Formaldehyde • Perbenzoic acid, 3-chloro • Acetate, sodium • Ba(ClO3)2 • Butadiene, 1-OR • Butadiene, 2-OR • Danishefsky diene • Epoxide • CH2=C(OLi)2 • DHP • |