334670-39-2Relevant articles and documents
Total syntheses of four metabolites of 15-F2t-isoprostane
Durand, Thierry,Guy, Alexandre,Henry, Olivier,Vidal, Jean-Pierre,Rossi, Jean-Claude,Rivalta, Claudia,Valagussa, Anna,Chiabrando, Chiara
, p. 809 - 819 (2007/10/03)
Total syntheses are described of the methyl esters of enantiomers of two major urinary metabolites of 15F2t-isoprostane - 2,3-dinor-5,6-dihydro-15F2t-isoprostane 1 and 2,3-dinor15F2t-isoprostane 2 - together with other, related, putative metabolites (15R)/(15S)-2,3-dinor-5,6,13,14-tetrahydro-15F2tisoprostane 3 and 2,3-dinor-5,6,13,14-tetrahydro-15-oxo 15F2t-isoprostane 4. The synthesis, starting from diacetone d-glucose, includes as its main steps a radical cyclization reaction of highly functionalized precursors, followed by Wittig and/or Horner-Wadsworth-Emmons elongation using phosphorus synthons. The compounds synthesized here have been used as reference compounds for studying the metabolism of 15F2t-isoprostane and ent-15F2t-isoprostane.