Phosphate esters. Part I. The synthesis of phenolic isoprenoids from allylic phosphates

Abstract

The synthesis of a series of allyl diphenyl phosphates is described. Reaction of these phosphate esters with a variety of phenols has been studied. The products are usually coumarans or chromans, and the method has been used for the synthesis of phenolic natural products containing isoprenoid residues. In particular, the reaction of 2,3,5-trimethylquinol with phytyl diphenyl phosphate gave α-tocopherol in excellent yield.

These experiments establish that allylic phosphate esters can function as efficient alkylating agents in chemical systems. They also simulate the role played by pyrophosphate esters in biological systems and demonstrate the chemical feasibility of biogenetic hypotheses which have been suggested.