Total synthesis of Pancratistatin:
| Reference: | Trost, B. M.; Pulley, S. R. J. Am. Chem. Soc. 1995, 117, 10143. DOI |
| Reactions: | Cu-Aryl+Allyl-X • Allyl-X+Cu-R • CompE+-Allyl carbonate/Azide+Cu-R • Mg-R → Cu-R • Sulfite → Sulfate • Allyl-OAc → Allyl-N3 (Pd) • Aryl-H → Aryl-Br • Amine → Isocyanate • Li/Br → Li-Aryl • Alkyl-X → Alkyl-OC(O)R • O-Me → O-H (phenol) • O-H → O-C(O)OR • Alkene → Diol-1,2 • O-H → O-SiEt3 • Diol-1,2 → Sulfite • O-SiEt3 → O-H • Azide → Amine • Staudinger • Li-Aryl+Isocyanate • Isocyanate+Li-R • Lactam-6 • CompE+-ArBr/Isocyanate+M-R • O-C(O)R → O-H • Ketal → Diol-1,2 • |
| Reagents: | BuLi(n) • O=C(OMe)Cl • PdCl(Allyl) • Chiral catalyst (phosphine) • Azide, trimethylsilyl • Aryl-MgX • CuCN • OsO4, NMO • SiEt3-OTf • NBS • PMe3 • Fluoride, R4N+ • SOCl2 • RuCl3 • Benzoate, cesium • Carbonate, potassium • Iodide, lithium • Periodate, sodium • Trost bisphosphine • Cl2 • DMF (solvent) • DMF (solvent) • Aryl-Li • BuLi(tert) • |