Total syntheses of four metabolites of 15-F-2t-isoprostane

Total syntheses are described of the methyl esters of enantiomers of two ma jor urinary metabolites of 15F(2t)-isoprostane -2,3-dinor-5,6-dihydro-15F(2 t)-isoprostane 1 and 2,3-dinor15F(2t)-isoprostane 2 - together with other, related, putative metabolites (15R)/(15S)-2,3-dinor-5,6,13,14-tetrahydro-15 F(2t)- isoprostane 3 and 2,3-dinor-5,6,13,14-tetrahydro-15-oxo15F(2t)-isopr ostane; 4, The synthesis, starting from diacetone d-glucose, includes as it s main steps a radical cyclization reaction of highly functionalized precur sors, followed by Wittig and/or Horner-Wadsworth-Emmons elongation using ph osphorus synthons. The compounds synthesized here have been used as referen ce compounds for studying the metabolism of 15F(2t)-isoprostane and ent-15F (2t)-isoprostane.