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Total synthesis of Resolvin E1

✍ Scribed by Melissa Allard; Keith Barnes; Xuemei Chen; Yiu-Yin Cheung; Bryan Duffy; Charles Heap; John Inthavongsay; Matthew Johnson; Ravi Krishnamoorthy; Chris Manley; Stephan Steffke; Deepu Varughese; Ruifang Wang; Yi Wang; C.E. Schwartz

Publisher
Elsevier Science
Year
2011
Tongue
French
Weight
449 KB
Volume
52
Category
Article
ISSN
0040-4039

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✦ Synopsis

The enantioselective total synthesis of Resolvin E1 (RvE1), a naturally occurring small molecule mediator of inflammation resolution, is reported. Two routes are presented, both modular and convergent in nature, with an excellent control of all stereocenters. The C12-and C18-hydroxy groups are derived from (S)glycidol while the C5-hydroxy group is installed via enantioselective reduction of a ketone precursor. Both the cis-alkenes are introduced with excellent control by the reduction of a late-stage bis-alkyne intermediate. The synthetic disconnections are very amenable to analog preparation, and further modifications to the chemistry have allowed for scale-up and First in Man testing of this novel pro-resolution molecule.

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