Attempted synthesis of a vinylog of chloramphenicol

Applying essentially the synthetic procedures of Long and Troutman, which led to chloramphenicol, we have attempted to synthesize a vinylog of the antibiotic in order to study the application of the theory of vinylogy to pharmacological results. However, failure to achieve the desired synthesis has suggested that even chemically the theory does not hold entirely, especially in regard to an apparently high specificity of structure which allows monohydroxymethylation in certain chloramphenicol intermediates and not in their vinylogs.