Saegusa–Ito oxidation

[1] The reaction as originally reported involved formation of a silyl enol ether followed by treatment with palladium(II) acetate and benzoquinone to yield the corresponding enone.

[3][4] Since the reaction typically employs near-stoichiometric amounts of palladium and is therefore often considered too expensive for industrial usage, some progress has been made in the development of catalytic variants.

[11] Yong Qiang Tu's synthesis of the Alzheimer's disease medication galantamine likewise used this reaction in the presence of an acid-sensitive acetal group.

[14] The vast majority of improvements to this reaction have focused on rendering the transformation catalytic with respect to the palladium salt, primarily due to its high cost.

The original conditions, though technically catalytic, still require 50 mol% of palladium(II) acetate, raising the cost to prohibitively high levels for large scale syntheses.

[15] This method suffers from long reaction times and often produces significantly lower yields than the stoichiometric equivalent as showcased in the synthesis of platyphillide by Nishida.

[17] This latter method has enjoyed greater success as a synthetic tool, most notably in the Shibasaki total synthesis of the famous poison strychnine.