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Total Synthesis and Absolute Stereochemical Assignment of (−)-Communesin F

机译:(-)-Communesin F的全合成和立体化学绝对分配

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摘要

A concise asymmetric total synthesis of (−)-communesin F (6% overall yield in the longest linear sequence of 19 steps) is described. It features an unprecedented intramolecular oxidative coupling strategy for the elaboration of the requisite spiro-fused indoline moiety. Other notable elements are the use of TBS-protected (S)-phenylglycinol as a chiral auxiliary to induce the asymmetric formation of the spiro-fused indoline part, the mesylate-mediated formation of its G ring, and the introduction of the A ring at the final stage via intramolecular Staudinger reaction. This intramolecular Staudinger reaction proceeded smoothly at 80 °C, providing an additional example illustrating that twisted amides are more reactive than simple amides. Along with the total synthesis, we were able to assign the absolute configuration of natural communesin F as 6R,7R,8R,9S,11R.
机译:描述了(-)-表素F的简明不对称总合成(在19个步骤的最长线性序列中,总产率为6%)。它具有史无前例的分子内氧化偶联策略,可用于精制必要的螺二氢吲哚化合物。其他值得注意的元素是使用TBS保护的(S)-苯基甘氨醇作为手性助剂来诱导螺-稠合的吲哚啉部分的不对称形成,甲磺酸酯介导的G环的形成以及A环的引入通过分子内斯陶丁格反应的最后阶段。分子内斯陶丁格反应在80°C下顺利进行,提供了另一个实例,说明扭曲的酰胺比简单的酰胺更具反应性。随着总的合成,我们能够将天然的共产蛋白F的绝对构型分配为6R,7R,8R,9S,11R。

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  • 来源
    《Journal of the American Chemical Society》 |2010年第38期|p.13226-13228|共3页
  • 作者单位

    State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China;

  • 收录信息 美国《科学引文索引》(SCI);美国《工程索引》(EI);美国《生物学医学文摘》(MEDLINE);美国《化学文摘》(CA);
  • 原文格式 PDF
  • 正文语种 eng
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  • 入库时间 2022-08-18 00:50:24

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