Synthesis of Fluorine-Containing Analogues of 1-Lysoglycerophospholipids via Horner–Wadsworth–Emmons Reaction

Michiyasu Nakao; Kazue Tanaka; Syuji Kitaike; Shigeki Sano

doi:10.1055/s-0036-1588826

Synthesis, Table of Contents

Synthesis 2017; 49(16): 3654-3661
DOI: 10.1055/s-0036-1588826

paper

Synthesis of Fluorine-Containing Analogues of 1-Lysoglycerophospholipids via Horner–Wadsworth–Emmons Reaction

Michiyasu Nakao

Graduate School of Pharmaceutical Sciences, Tokushima University, Sho-machi, Tokushima 770-8505, Japan Email: ssano@tokushima-u.ac.jp

,

Kazue Tanaka

Graduate School of Pharmaceutical Sciences, Tokushima University, Sho-machi, Tokushima 770-8505, Japan Email: ssano@tokushima-u.ac.jp

,

Syuji Kitaike

Graduate School of Pharmaceutical Sciences, Tokushima University, Sho-machi, Tokushima 770-8505, Japan Email: ssano@tokushima-u.ac.jp

,

Shigeki Sano*

Graduate School of Pharmaceutical Sciences, Tokushima University, Sho-machi, Tokushima 770-8505, Japan Email: ssano@tokushima-u.ac.jp

› Author Affiliations

Abstract

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Abstract

An efficient method of synthesizing fluorine-containing analogues of 1-lysoglycerophospholipids (1-LPLs) by introducing a palmitoyl moiety starting from bis(2,2,2-trifluoroethyl)phosphonoacetate (Still–Gennari reagent) is described. The method effectively employs Horner–Wadsworth–Emmons reagents as masked 1-LPL derivatives to prepare a series of analogues of 1-lysophosphatidic acid (1-LPA), 1-lysophosphatidylethanolamine (1-LPE), and 1-lysophosphatidylcholine (1-LPC).

Key words

lysoglycerophospholipid - Horner–Wadsworth–Emmons reaction - fluorine - lysophosphatidic acid - lysophosphatidylethanolamine - lysophosphatidylcholine

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References

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