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Total synthesis of Deoxy-Penostatin A:
Reference: Snider, B. B.; Liu, T. J. Org. Chem. 2000, 65, 8490-8498. DOI
Keywords: 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 • 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 • Dess-Martin • NaH • Carbonate, potassium • Acetate, sodium • LiNiPr2 • BuLi(sec) • Epoxide • BuLi(sec) •

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