Efficient synthesis of 40-and 48-membered tetraether macrocyclic bisphosphocholines

An efficient route toward the synthesis of unsaturated (bis-diacetylenic) and saturated 40- and 48-membered macrocyclic bisphosphocholines has been developed using 2-phenyl-5-hydroxy-1,3-dioxane as a common glycerol synthon. Ring closure was accomplished using either high dilution Glaser oxidation or [(Cy3P)(2)Ru=CHPh]Cl-2-catalyzed olefin metathesis conditions. Deprotection of benzyl ethers using trimethyisilyl iodide (TMS I) in the presence of diacetylenic moieties has also been demonstrated for the first time.