TY - JOUR
T1 - First total synthesis of the pro-resolving lipid mediator 7(S),12(R),13(S)-Resolvin T2 and its 13(R)-epimer
AU - Rodriguez, Ana R.
AU - Spur, Bernd W.
N1 - Publisher Copyright:
© 2020 Elsevier Ltd
PY - 2020/5/14
Y1 - 2020/5/14
N2 - 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.
AB - 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.
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U2 - 10.1016/j.tetlet.2020.151857
DO - 10.1016/j.tetlet.2020.151857
M3 - Article
AN - SCOPUS:85082672607
SN - 0040-4039
VL - 61
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 20
M1 - 151857
ER -