...
  • 主题
高级搜索  >
历史搜索 清空历史
首页> 外文期刊>The Journal of Organic Chemistry >Stereoselective Synthesis of Isochromanones by an Asymmetric Ortho-Lithiation Strategy: Synthetic Access to the Isochromanone Core of the Ajudazols
【24h】

Stereoselective Synthesis of Isochromanones by an Asymmetric Ortho-Lithiation Strategy: Synthetic Access to the Isochromanone Core of the Ajudazols

机译：通过不对称邻位锂化策略立体选择性合成异色满酮：合成对Ajudazols的异色满酮核心的访问

获取原文
获取原文并翻译 | 示例
   

获取外文期刊封面封底 >>

       
页面导航
  • 摘要
  • 著录项
  • 相似文献
  • 相关主题

摘要

Full details, on the design, development, and application of a highly stereoselective strategy for the synthesis of isochromanones are reported. The method is based on an asymmetric ortho lithiation with aldehyde electrophiles and utilizes the chiral memory of a preoriented atropisomeric amide axis for stereocontrol. For direct transformation of sterically hindered amides to isochromanones, efficient and mild one-pot protocols involving either Q-alkylation or acidic microwave activation were developed. The procedures may be applied also to highly futictionalized as well as stereochemically complex and sensitive substrates and demonstrate a high protective group tolerance. Furthermore, asymmetric crotylborations of axially chiral amides were studied in detail. These methodologies enable a general access to all possible stereoisomers of hydroxyl-isochromanones with up to three contiguous stereocenters. The true applicability of our approach was finally demonstrated by synthesis of the authentic anti,anti-configured isochromanone core of the ajudazols, highly potent inhibitors of the mitochondrial respiratory chain from myxobacteria.
机译：报告了有关异色酮合成的高立体选择性策略的设计，开发和应用的详细信息。该方法基于具有醛亲电试剂的不对称邻位锂化，并利用预取向的阻转异构酰胺轴的手性记忆进行立体控制。为了将位阻酰胺直接转化为异色酮，开发了涉及Q-烷基化或酸性微波活化的高效温和的一锅法。该程序也可用于高度官能化以及立体化学复杂和敏感的底物，并显示出较高的保护基耐受性。此外，详细研究了轴向手性酰胺的不对称巴豆基硼酸酯。这些方法论使人们能够普遍访问具有最多三个连续立体中心的羟基异色酮的所有可能的立体异构体。最后，通过粘胶体线粒体呼吸链的高效抑制剂ajudazols的真实抗，反构型异苯并二氢吡喃酮核心的合成，最终证明了我们方法的真正适用性。

著录项

相似文献

  • 外文文献
  • 中文文献
  • 专利
获取原文

客服邮箱：kefu@zhangqiaokeyan.com

京公网安备：11010802029741号 ICP备案号：京ICP备15016152号-6 六维联合信息科技 (北京) 有限公司©版权所有

  • 客服微信

  • 服务号