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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 • Criegee oxidation • Alkene cleavage • CarboxAcid → CarboxEster • Lactone → Orthoester • Lactone → Lactol • Orthoester → CarboxEster • Lactone-5 • Lactone-6 • O-H → O-THP • O-H → O-SO2R • Dehydrosulfonoxylation → EnoateEster • O-THP → O-H • Iodolactonization • Furst-Plattner diaxial • Lactone-5 • Wittig-methyl • Epoxidation, peracid • Henbest • CompOx-Alkene/Enone+Peracid • Dehydrohalogenation → Allyl-OR • Diels-Alder, EnoateEster • Furst-Plattner diaxial • CarboxAcid enolate+Epoxide • Epoxide+Enolate • CompRed-Aldehyde/CarboxEster+M-H • CarboxEster enolate+Aldehyde •
Reagents: Hydroxide, sodium • I2, KI • DBU • Hydroxide, sodium • OsO4 • Pb(OAc)4 • Diazomethane • BH(sBu3)-Li+ • Amberlite • Glycol • AlHiBu2 • PPh3=CH2 • TsOH • DHP • LiNiPr2, HMPA • Sulfonyl chloride, methane, NEt3 • DBU • Formaldehyde • Perbenzoic acid, 3-chloro • Acetate, sodium • Ba(ClO3)2 • Danishefsky diene • Epoxide • CH2=C(OLi)2 • HMPA (solvent) •

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