Total syntheses of four metabolites of 15-F2t-isoprostane

Article abstract of DOI:10.1002/1099-0690(200102)2001:4<809::AID-EJOC809>3.0.CO;2-6

Total syntheses are described of the methyl esters of enantiomers of two major urinary metabolites of 15F_2t-isoprostane - 2,3-dinor-5,6-dihydro-15F_2t-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-15F_2tisoprostane 3 and 2,3-dinor-5,6,13,14-tetrahydro-15-oxo 15F_2t-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 15F_2t-isoprostane and ent-15F_2t-isoprostane.