Mesitoylated model compounds

General method for determining relative configuration of mono-THF acetogenins by correlation of H chemical shifts with mesitoylated model compounds. 

A year later, Cassady published the synthesis and study of a set of model compounds representing the full spectrum of possible stereochemical relationships in dihydroxylated mono-THF acetogenins. Six mesitoylated compounds (23a-f, Fig. 13) were synthesized and subjected to H NMR spectroscopic studies. In these bis-mesitoates, good correlation between the relative configuration and the chemical shifts of selected protons was observed (Table 6). Specifically, It was found that ... 

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