Abstract
Oxylipins are formed in vivo from polyunsaturated fatty acids (PUFAs). A large structural
variety of compounds is grouped under the term oxylipins, which differ from their
formation mechanism (involving enzymes or not), as well as their chemical structures
(cyclopentane, tetrahydrofuran, hydroxylated-PUFA, etc.). All structures of oxylipins
are of great biological interest. Directly correlated to oxidative stress phenomenon,
non-enzymatic oxylipins are used as systemic and/or specific biomarkers in various
pathologies, and more especially, they were found to have their own biological properties.
Produced in vivo as a non-separable mixture of isomers, their total synthesis is a
keystone to answer biological questions. In this work, the total synthesis of three
non-enzymatic oxylipins derived from docosahexaenoic acid (DHA) and docosapentanoic
acid (DPAn-3) is described using a unique and convergent synthetic strategy.
Key words
total synthesis - oxidative stress - biomarkers - neuroprostanes - non-enzymatic oxylipins
