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 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.
Patwardhan
A P
AP
Department of Chemistry, Wetherill Laboratory of Chemistry, Purdue University, West Lafayette, Indiana 47907-1393, USA.
Thompson
D H
DH
D000114:Acetylene / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D001105:Archaea / Q000737:chemistry; D008563:Membrane Lipids / Q000737:chemistry; D018716:Molecular Mimicry; D010713:Phosphatidylcholines / Q000138:chemical synthesis*
D008563:Membrane Lipids; D010713:Phosphatidylcholines; D000114:Acetylene