Conversion of Shikimic Acid to 5-Enolpyruvylshikimate 3-Phosphate

Article abstract of DOI:10.1021/jo00351a015

The synthesis of (-)-5-enolpyruvylshikimate 3-phosphate (3), a principle metabolite in the shikimic acid pathway, has been accomplished in 22percent overall yield from the known acetonide 6.A key intermediate in the synthesis is diester 9.Direct cyclization of this material affords lactone 10 and distinguishes the three hydroxyl groups of the shikimate nucleus.The phosphate moiety is introduced efficiently with tetrabenzyl pyrophosphate, followed by deprotection with trimethylsilyl bromide. (-)-5-Enolpyruvylshikimic acid (4), a secondary metabolite in the shikimate/chlorismate pathway, is formed on hydrolysis of 9.