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

The 6-(poly)prenyl-substituted polyprenols 7, 9, 11, and 13 were synthesize d: (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-butyldiphenylsi loxy-5-iodo-3-methyl-2-pentene, via beta-keto ester 35, and (4) 13 from ger aniol 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. (C) 1999 Elsevier Science Ltd. All rights r eserved.