New aspects of the Hunsdiecker–Barton halodecarboxylation—syntheses of phospha-shikimic acid and derivatives

We report an efficient synthetic approach to phospha-isosteres of important intermediates of the shikimic acid pathway by the application of the Hunsdiecker–Barton halodecarboxylation to cyclohexenylcarboxylic acids. As examples, phospha-shikimic acid, its 3-dehydro derivative and the respective monomethyl esters were synthesized. The approach has proven equally useful in the synthesis of isosteres of the antiviral agent oseltamivir.