Total synthesis of Wodeshiol:
| Reference: | Han, X.; Corey, E. J. Org. Lett. 1999, 1, 1871–1872. DOI |
| Reactions: | Enone → Enone-α-Halo • Li/Br → Li-Vinyl • Li-R → Sn-R • Sn-Vinyl oxidative coupling • Pd/Sn-Vinyl+Vinyl-X • Epoxidation, V • Epoxide → Tetrahydrofuran • Ether-5 • Bicyclo(330)-oxa • Enone → Allyl-OH (asym) • |
| Reagents: | Br2 • NEt3 • Corey oxazaborolidine • Chiral catalyst (amino-alcohol) • BH(Catechol) • BuLi(tert) • SnBu3-Cl • Pd(PPh3)4 • CuCl • CuCl2 • Hydroperoxide, tbutyl - V • TsOH·Py • |