Total synthesis of Verrucarol (partial):
| Reference: | Roush, W. R.; D'Ambra, T. E. J. Org. Chem. 1981, 46, 5045. DOI |
| Reactions: | Diels-Alder, EnoateEster • Bicyclo(221) • CarboxEster → CarboxAcid • CompRed-CarboxEster/Epoxide+M-H • Epoxidation, peracid • Wagner-Meerwein • Mechanism • Alkyl-X → Alkyl-SeR • Mechanism • CompNu-Alkyl-OH/Alkyl-OH+SeCN • Selenide → Selenoxide • Selenoxide-Ei → Ene • Baeyer-Villiger • Lactone-6 • Ozonolysis • Epoxide reduction • |
| Reagents: | Selenocyanate, o-nitrophenyl • PBu3 • Cyclopentadiene • Acrylate • BF3·OEt2 • AlH(OMe)3-Li+ • Perbenzoic acid, 3,5-dinitro • Perbenzoic acid, 3-chloro • Li°/H2NCH2CH2NH2 • O3 • Me2S • AlH4-Li+ • Perbenzoic acid, 3-chloro • Bicarbonate, sodium • |