213777-19-6Relevant articles and documents
Total Synthesis of the Eight Diastereomers of the Syn-Anti-Syn Phytoprostanes F1 Types I and II
El Fangour, Siham,Guy, Alexandre,Despres, Valerie,Vidal, Jean-Pierre,Rossi, Jean-Claude,Durand, Thierry
, p. 2498 - 2503 (2004)
Syntheses of the eight enantiomerically pure diastereomers of the syn-anti-syn phytoprostanes F1 types I and II are described starting from D- and L-glucose. Key steps include Wittig coupling, Horner Wadsworth Emmons (HWE) reactions, and enantioselective reduction of α,β -unsaturated ketones.
Total synthesis of phytoprostane F1 and its 16 epimer
El Fangour, Siham,Guy, Alexandre,Vidal, Jean-Pierre,Rossi, Jean-Claude,Durand, Thierry
, p. 2105 - 2108 (2007/10/03)
The first synthesis of the two enantiomers of phytoprostane F1 methyl ester 1 and 2 is described using the syn-anti-syn alcoxy ester 3 as starting material.
Syntheses and preliminary pharmacological evaluation of the two epimers of the 5-F2t-isoprostane
Durand, Thierry,Cracowski, Jean-Luc,Guy, Alexandre,Rossi, Jean-Claude
, p. 2495 - 2498 (2007/10/03)
The total synthesis of the 5-F2t-isoprostane 1 and its 5-epimer 2 from diacetone-D-glucose is described. We report preliminary data on the vascular properties of these compounds.
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.
Total synthesis of 4(RS)-F(4t)-isoprostane methyl ester
Durand, Thierry,Guy, Alexandre,Vidal, Jean-Pierre,Viala, Jacques,Rossi, Jean-Claude
, p. 3859 - 3862 (2007/10/03)
The first total synthesis of 4(RS)-F(4t)-isoprostane methyl ester 1 is described using diacetone-D-glucose as starting material. This new isoprostane (neuroprostane) would be very useful in neurological studies as a potent lipid peroxidation in
Total synthesis of ent-15(RS)-2,3-dinor-5,6-dihydro-8-epi-PGF2α.
Guy, Alexandre,Durand, Thierry,Roland, Arlene,Cormenier, Emmanuelle,Rossi, Jean-Claude
, p. 6181 - 6184 (2007/10/03)
The first total synthesis of ent-15(RS)-2,3-dinor-5,6-dihydro-8-epi- PGF2α 1 is described using diacetone-D-glucose as starting material. The major urinary metabolite of the isoprostane 8-epi-PGF2α is 2,3-dinor-5,6- dihydro-8-epi-PGF2α, which is a potent lipid peroxidation index to obtain an integrated assessment of oxidative stress in humans.