First total synthesis of pro-resolving and tissue-regenerative Maresin sulfido-conjugates

Abstract

The first stereospecific total synthesis of the pro-resolving and tissue-regenerative Maresin sulfido-conjugates: 13R,14S-MCTR1, 13R,14S-MCTR2 and 13R,14S-MCTR3, derived from docosahexaenoic acid, has been achieved. The key intermediate 13S,14S-epoxy-Maresin methyl ester was synthesized using a chiral pool strategy starting from 2-deoxy-d-ribose. Wittig reactions, selective epoxide formation and epoxide opening with glutathione, l-cysteinylglycine and l-cysteine methyl ester hydrochloride respectively, were the key steps in the synthesis.