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Total Synthesis of 15‐F 2t ‐Isoprostane by Using a New Oxidative Cyclization of Distonic Radical Anions as the Key Step
Author(s) -
Jahn Ullrich,
Dinca Emanuela
Publication year - 2008
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200802139
Subject(s) - cyclopentane , chemistry , alkylation , aldol reaction , epimer , radical cyclization , total synthesis , yield (engineering) , stereochemistry , medicinal chemistry , organic chemistry , catalysis , materials science , metallurgy
Cyclization/oxygenation and alkylation reactions : A concise total synthesis of 15‐F 2t ‐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.