Tetrahedron Letters ( IF 1.8 ) Pub Date : 2020-03-19 , DOI: 10.1016/j.tetlet.2020.151857 Ana R Rodriguez 1 , Bernd W Spur 1
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.
中文翻译:
亲分解脂质介体7(S),12(R),13(S)-Resolvin T2及其13(R)-受体的第一全合成。
亲分解脂质介体7(S),12(R),13(S)-Resolvin T2 [7(S),12(R),13(S)-RvT2]及其13(描述了衍生自n-3二十二碳五烯酸(n-3 DPA)的R 1-末端。使用手性池策略引入手性中心,通过全合成得到7(S),12(R),13(S)-RvT2及其13(R)-顶基。C7由两个分子中的S -(-)-1,2,4-丁三醇生成,C12和C13中心分别由L-(+)-核糖和D-(-)-阿拉伯糖生成。顺式和反式Wittig反应,选择性脱保护和Dess-Martin高碘烷氧化是合成的关键步骤。