Total Synthesis of 15‐F2t‐Isoprostane by Using a New Oxidative Cyclization of Distonic Radical Anions as the Key Step

Total Synthesis of 15‐F2t‐Isoprostane by Using a New Oxidative Cyclization of Distonic Radical Anions as the Key Step

Cyclization/oxygenation and alkylation reactions: A concise total synthesis of 15‐F2t‐IsoP (see scheme) and its 15‐epimer, today used as the gold standard marker of oxidative stress in vivo, has been accomplished in 12 steps in 14 % overall yield by applying a vinylogous aldol addition, a new oxidat...

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Veröffentlicht in:Chemistry : a European journal 2009, Vol.15 (1), p.58-62
Hauptverfasser: Jahn, Ullrich, Dinca, Emanuela
Format: Artikel
Sprache:eng
Schlagworte:
Anions - chemistry
Cyclization
electron transfer
Electron Transport
Isoprostanes - chemical synthesis
Isoprostanes - chemistry
Prostaglandins - chemistry
prostanoids
radical ions
total synthesis
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Zusammenfassung:Cyclization/oxygenation and alkylation reactions: A concise total synthesis of 15‐F2t‐IsoP (see scheme) and its 15‐epimer, today used as the gold standard marker of oxidative stress in vivo, has been accomplished in 12 steps in 14 % overall yield by applying a vinylogous aldol addition, a new oxidative radical anion cyclization/oxygenation sequence to construct the cyclopentane core, and an acetylide alkylation as the key steps.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.200802139