Synthesis of 6-(poly)prenyl-substituted polyprenols and their phosphates

Article abstract of DOI:10.1016/S0040-4020(99)00057-5

The 6-(poly)prenyl-substituted polyprenols 7, 9, 11, and 13 were synthesized: (1) 7 from 2-geranyl-farnesal and methyl 4-bromo-3-methyl-2- butenoate, (2) 9 from 2-prenyl-geranyl bromide and ethyl acetoacetate, via ketone 29, (3) 11 from ethyl acetoacetate, geranyl bromide, and (E)-1-t- butyldiphenylsiloxy-5-iodo-3-methyl-2-pentene, via β-keto ester 35, and (4) 13 from geraniol by acid catalyzed condensation. These highly branched polyprenols 7, 9, 11, and 13 were transformed into the corresponding disodium phosphates 8, 10, 12, and 14, respectively.