Total Synthesis of the Marine Alkaloid Discoipyrrole C via the MoOPH-Mediated Oxidation of a 2,3,5-Trisubstituted Pyrrole,Journal of Natural Products

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Total Synthesis of the Marine Alkaloid Discoipyrrole C via the MoOPH-Mediated Oxidation of a 2,3,5-Trisubstituted Pyrrole
Journal of Natural Products ( IF 3.3 ) Pub Date : 2017-11-28 00:00:00 , DOI: 10.1021/acs.jnatprod.7b00872
Qiao Yan ₁ , Xiang Ma ₁ , Martin G. Banwell ₁ , Jas S. Ward ₁

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A total synthesis of the marine alkaloid discoipyrrole C (3) is described. In the pivotal step, the 2,3,5-trisubstituted pyrrole 19 was treated with MoOPH in the presence of MeOH, and the resulting methoxylated 1,2-dihydro-3H-pyrrol-3-one 20 subjected to reaction with potassium carbonate in MeOH then trifluoroacetic acid and H₂O. This gave a mixture of target 3 and its dehydration product, and the structure of the former compound was confirmed by single-crystal X-ray analysis.

中文翻译：

通过MoOPH介导的2,3,5-三取代的吡咯的氧化反应，全过程合成海洋生物碱DiscoipyrroleC。

描述了海洋生物碱盘二吡咯C（3）的全合成。在关键步骤中，在MeOH的存在下用MoOPH处理2,3,5-三取代的吡咯19，并使所得的甲氧基化的1,2-二氢-3 H-吡咯-3-酮20与碳酸钾反应在MeOH中然后在三氟乙酸和H ₂ O中洗脱。这得到目标3及其脱水产物的混合物，并且通过单晶X射线分析确认了前一种化合物的结构。

更新日期：2017-11-28

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