Smith’s total synthesis

Scheme 6.3 Smith s total synthesis of (-)-echinosporin from L-ascorbic acid.

Paquette was one of the first to apply the Wacker oxidation in the total synthesis. In his synthesis of 18-oxo-3-virgene, a constituent of the waxy surface resins of tobacco, a Wacker oxidation was deployed to convert a terminal alkene to the corresponding methyl ketone.59 In an efficient total synthesis of ( )-laurene (77), alkene 75 was oxidized to keto-aldehyde 76 at ambient temperature.60 In Smith s total synthesis of calyculin, a modified Wacker oxidation with substoichiometric cupric acetate transformed terminal alkene 78 to methyl ketone 79 without concurrent acetonide hydrolysis.61,62... 

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