Synthesis of 2-Polyprenyl-Substituted Polyprenols and Their Conversion into Phosphates

Highly Branched polyprenols, {(6E)-2-[(2E)-3,7-dimethyl-2,6-octadienyl]-7,11-dimethyl-3-methylene-6,10-dodecadien-1-ol and (6E,10E)-2-[(2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrienyl]-7,11,15-trimethyl-3-methylene-6,10,14-hexadecatrien-1-ol}, were synthesized (1) from diethyl malate, geranyl bromide, and homogeranyl iodide, and (2) from ethyl acetoacetate and geranyl (or farnesyl) bromide. These alcohols were transformed into disodium phosphates, which have been postulated to be primitive lipids in the evolution of membranes.

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