Chemistry A general approach to cyclopentenone neuroprostanes: total synthesis of 14-A4-NeuroP

Dedicated to the Morrow’s group in occasion of the first anniversary of a fruitful collaboration. Neuroprostanes are generated both in vitro and in vivo by the free radical promoted oxidation of docosahex-aenoic acid (DHA). The phenomenon, commonly referred to as lipid peroxidation, has long been associated with neurodegenerative diseases, such as Alzheimer and Parkinson. In order to set diagnostic tests for these pathologies, we embarked in the synthesis of cyclopentenone neuroprostanes, to be used as biomarkers in vivo. The synthesis of 14-A4-NeuroP (1) was realized through an orginal approch based on a highly stereos-elective Julia olefination and, due to its versatility, can be considered a general approach to cyclopentenone neuroprostanes.