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The Shortest Strategy for Generating Phosphonate Prodrugs by Olefin Cross‐Metathesis – Application to Acyclonucleoside Phosphonates
Author(s) -
Pradère Ugo,
Clavier Hervé,
Roy Vincent,
Nolan Steven P.,
Agrofoglio Luigi A.
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201101111
Subject(s) - phosphonate , prodrug , chemistry , olefin metathesis , catalysis , carbene , metathesis , olefin fiber , combinatorial chemistry , ruthenium , organic chemistry , stereochemistry , biochemistry , polymerization , polymer
A short synthetic route to phosphonate prodrugs by olefin cross‐metathesis, which uses either (acyloxymethyl) or (hexadecyloxypropyl) allylphosphonate building blocks is described. A study of eight ruthenium catalysts including the Ru–indenylidene catalyst, which bears the N‐heterocyclic carbene 1,3‐bis(2,6‐diisopropylphenyl)‐4,5‐dihydroimidazol‐2‐ylidene, was undertaken. This method was applied to the synthesis of acyclonucleoside phosphonate prodrugs. This strategy is appealing for further uses in pharmaceutical and medicinal research.