Journal
TETRAHEDRON LETTERS
Volume 56, Issue 25, Pages 3936-3940Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2015.04.131
Keywords
Maresin sulfido-conjugates; Total synthesis; Inflammation resolution; Tissue-regeneration; Wittig reaction; Chiral pool
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Funding
- DOD [A5073084P1]
- NJCBIR
- Governor's Council on Autism
- Office of Patent & Licensing UMDNJ-UMDNJ Foundation
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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. (C) 2015 Elsevier Ltd. All rights reserved.
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