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First total synthesis of the pro-resolving lipid mediator 7(S),12(R),13(S)-Resolvin T2 and its 13(R)-epimer.


ABSTRACT: The first total synthesis of the pro-resolving lipid mediator 7(S),12(R),13(S)-Resolvin T2 [7(S), 12(R), 13(S)-RvT2] and its 13(R)-epimer, derived from n-3 docosapentaenoic acid (n-3 DPA), are described. 7(S), 12(R), 13(S)-RvT2 and its 13(R)-epimer were obtained by total synthesis using a chiral pool strategy to introduce the chiral centers. C7 was generated from S-(-)-1,2,4-butanetriol in both molecules and the C12 and C13 centers were generated from L-(+)-ribose and D-(-)-arabinose respectively. Cis and trans-selective Wittig reactions, selective deprotections, and Dess-Martin periodinane oxidation were the key steps in the syntheses.

SUBMITTER: Rodriguez AR 

PROVIDER: S-EPMC7454203 | biostudies-literature | 2020 May

REPOSITORIES: biostudies-literature

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First total synthesis of the pro-resolving lipid mediator 7(<i>S</i>),12(<i>R</i>),13(<i>S</i>)-Resolvin T2 and its 13(<i>R</i>)-epimer.

Rodriguez Ana R AR   Spur Bernd W BW  

Tetrahedron letters 20200319 20


The first total synthesis of the pro-resolving lipid mediator 7(<i>S</i>),12(<i>R</i>),13(<i>S</i>)-Resolvin T2 [7(<i>S</i>), 12(<i>R</i>), 13(<i>S</i>)-RvT2] and its 13(<i>R</i>)-epimer, derived from n-3 docosapentaenoic acid (n-3 DPA), are described. 7(<i>S</i>), 12(<i>R</i>), 13(<i>S</i>)-RvT2 and its 13(<i>R</i>)-epimer were obtained by total synthesis using a chiral pool strategy to introduce the chiral centers. C7 was generated from <i>S</i>-(-)-1,2,4-butanetriol in both molecules and the  ...[more]

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