Total synthesis of 4-F3t-neuroprostane and its 4-epimer

The first synthesis of 4-F-3t-Neuroprostane 1a and its 4-epimer is described. This molecule presents an important contribution to the study of neuronal oxidative stress in DHA-omega 3 depleted brain. The key step involves the introduction of two unsaturated side chains into the chiral polyfunctional cyclopentane 4 via E selective HWE reaction and Z selective Wittig olefination for alpha and omega chains, respectively. (C) 2009 Elsevier Ltd. All rights reserved.