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. 2013 Apr 5;15(7):1424-7.
doi: 10.1021/ol400484u. Epub 2013 Mar 19.

Stereocontrolled total synthesis of the potent anti-inflammatory and pro-resolving lipid mediator resolvin D3 and its aspirin-triggered 17R-epimer

Jeremy W Winkler  1 , Jasim Uddin, Charles N Serhan, Nicos A Petasis
Affiliations

Stereocontrolled total synthesis of the potent anti-inflammatory and pro-resolving lipid mediator resolvin D3 and its aspirin-triggered 17R-epimer

Jeremy W Winkler et al. Org Lett. .

Abstract

The first total synthesis of stereochemically pure resolvin D3 and aspirin-triggered resolvin D3 is reported. These enzymatic metabolites of docosahexaenoic acid (DHA) have potent anti-inflammatory and pro-resolving actions. The convergent synthetic strategy is based on enantiomerically pure starting materials, and it is highly stereocontrolled.

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Figures

Scheme 1
Scheme 1
Biosynthesis of resolvin D3 and AT-resolvin D3
Scheme 2
Scheme 2
Retrosynthetic analysis of resolvin D3
Scheme 3
Scheme 3
Synthesis of key intermediates 5, 9 and 10
Scheme 4
Scheme 4
Synthesis of RvD3 from intermediates 5, 9 and 10
Scheme 5
Scheme 5
Total synthesis of AT-resolvin D3 (2)
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