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Efficient synthesis of 40- and 48-membered tetraether macrocyclic bisphosphocholines
1Department of Chemistry, Wetherill Laboratory of Chemistry, Purdue University, West Lafayette, Indiana 47907-1393, USA.
Organic Letters
|July 25, 2000
Abstract:
An efficient route toward the synthesis of unsaturated (bis-diacetylenic) and saturated 40- and 48-membered macrocyclic biphosphocholines 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 of [(Cy3P)2RU==CHPh]Cl2-catalyzed olefin metathesis conditions. Deprotection of benzyl ethers using trimethylsilyl iodide (TMS-I) in the presence of diacetylenic moieties has also been demonstrated for the first time.