Total synthesis of Deoxy-Penostatin A:
| Reference: | Snider, B. B.; Liu, T. J. Org. Chem. 2000, 65, 8490-8498. DOI |
| Reactions: | Alkyl-X → Alkyl-ONO2 • Kornblum oxidation • Alkyl-X → Aldehyde • Li-Phosphonate+Lactone • Diels-Alder, Aldehyde • Ether-6 • Lactone-6 • Ketone epimerization • HWE → Enone (intram) • Cyclohexenone • Bicyclo(430) • Wittig-methyl alkylation • Wittig-alkyl → Ene-trans • Aldehyde azaenolate+Aldehyde • Alkyl-OH → Ketone • O-H → O-C(O)R • Alkyl-X → Alkyl-I • Finkelstein reaction • |
| Reagents: | Bromoacetate • Iodide, sodium • AgNO3 • Y(OTf)3 • Pyridine, 2,6-di-tBu • LiCH2-PO(OMe)2 • Dess-Martin • NaH • Carbonate, potassium • Acetate, sodium • LiNiPr2 • BuLi(sec) • Epoxide • BuLi(sec) • |