Synthesis of a Phosphinate Analogue of the Antitumour Phospholipid Edelfosine

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Abstract

The first concise synthesis of a phosphinate analogue of the antitumour ether phospholipid edelfosine is described. The key synthetic step comprised the free-radical addition reaction of phosphinic acid to a functionalised allyl ether, to incorporate the hydrophobic tail into a monosubstituted Hphosphinic acid. The hydrophilic head group was then added by using a silyl phosphonite based Michael addition. The reported synthetic study lays the groundwork for the synthesis of modified phosphinate phospholipid derivatives to facilitate investigations on their biological activity as membranetargeting antitumour agents.

Bibliographical metadata

Original languageEnglish
Pages (from-to)4996-5003
Number of pages7
JournalEuropean Journal of Organic Chemistry
DOIs
StatePublished - 2015