Total synthesis of Pinatol:
| Reference: | Hudlicky, T.; Price, J. D.; Rulin, F.; Tsunoda, T. J. Am. Chem. Soc. 1990,112, 9439-9440. DOI |
| Reactions: | Alkene → Diol-1,2 (asym) • Ketal → Diol-1,2 • Alkene → Diol-1,2 • Epoxidation, Peracid • Epoxidation, Peracid • Vinyl-Br → Vinyl-H • Vinyl-Br → Vinyl-H • Epoxide+M-OR • Epoxide → Diol • Alkene → Diol-1,2 • Ketal → Diol-1,2 • Stereoconvergent • |
| Reagents: | Enzyme • Perbenzoic acid, 3-chloro • Al2O3 • HOMe (react) • AlH4-Li+ • OsO4, NMO • HCl, H2O • OsO4, NMO • AlH4-Li+ • Perbenzoic acid, 3-chloro • Acetone (react) • Al2O3 • HOMe (react) • HCl, H2O • |