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

0332943 - ÚOCHB 2010 RIV DE eng J - Journal Article
Jahn, Ullrich - Dinca, E.
Total Synthesis of 15-F2t-Isoprostane by Using a New Oxidative Cyclization of Distonic Radical Anions as the Key Step.
Chemistry - A European Journal. Roč. 15, č. 1 (2009), s. 58-62. ISSN 0947-6539. E-ISSN 1521-3765
Grant - others:DFG(DE) Ja896/3-1
Institutional research plan: CEZ:AV0Z40550506
Keywords : cyclization * electron transfer * prostanoids * radical ions
Subject RIV: CC - Organic Chemistry
Impact factor: 5.382, year: 2009

The shortest total synthesis of the major human cyclic lipid peroxidation metabolite, 15-F2t-IsoP in twelve steps and 14% overall yield is reported. Keysteps are a vinylogous aldol addition to construct the C7-C20 skeleton, an oxidative electron transfer-induced radical anion 5-exo cyclization to access the cyclopentane subunit and an acetylide alkylation to assemble the full skeleton of the natural product.
Permanent Link: http://hdl.handle.net/11104/0178054