Total synthesis of Deoxy-Pancratistatin:
| Reference: | Acena, J. L.; Arjona, O.; Leon, L.; Plumet, J. Org. Lett. 2000, 2, 3683-3686. DOI |
| Reactions: | EneSulfone epoxidation, nucleophilic • Hydrogenation azide • Azide → Amine • Alkyl-X → Alkyl-N3 • Alkyl-SO2R → Alkyl-H • Li-Aryl+EneSulfone • EneSulfone+Li-R • ConjAdd Li-R • Lactam-6 • Li/Br → Li-Aryl • Ketal → Diol-1,2 • CarboxEster → CarboxAmide • O-H → O-Tf • Alkyl-OH → Alkyl-N3 • Alkene cleavage • Lactone-6 • Epoxide → Diol • |
| Reagents: | Hydroperoxide, tbutyl • BuLi(n) • Na(Hg) • Tf2O • RuCl3 • H2, Pd • Acetic acid, trifluoro • Carbonate, potassium • Azide, R4N+ • Periodate, sodium • EneSulfone • Aryl-Li • BuLi(n) • |