Bradyrhizose is an important component present in the lipopolysaccharide O-antigen side chain of Bradyrhizobium species (BTAil and ORS278 strains). It is perceived to function as a molecular signal that invokes the fixation of nitrogen in certain leguminous plants through a symbiotic process. As a structurally complex bicyclic sugar, bradyrhizose’s synthesis poses numerous challenges that have to be considered before studies on its biological properties can be investigated. The known literature synthesis employed 24 steps, and as a result we have developed a simpler and shorter synthetic scheme that utilizes the readily available D-glucose as a precursor and employs a radical reaction and ring closing metathesis to afford bradyrhizose in 14 steps with good overall yield (Scheme 1). The complete synthesis will be presented.

Concise total synthesis of Bradyrhizose from D-glucose

2019 Spring National Meeting

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