• 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 >Explorations of Caffeic Acid Derivatives: Total Syntheses of Rufescenolide, Yunnaneic Acids C and D, and Studies toward Yunnaneic Acids A and B
【24h】

Explorations of Caffeic Acid Derivatives: Total Syntheses of Rufescenolide, Yunnaneic Acids C and D, and Studies toward Yunnaneic Acids A and B

机译：咖啡酸衍生物的探索：决明烯内酯，云南酸C和D的总合成以及对云南酸A和B的研究

获取原文
获取原文并翻译 | 示例
           
页面导航
  • 摘要
  • 著录项
  • 相似文献
  • 相关主题

摘要

Yunnaneic acids A-D, isolated from the roots of Salvia yunnanensis, are hexameric (A and B) and trimeric (C and D) assemblies of caffeic acid that feature an array of synthetically challenging and structurally interesting domains. In addition to being caffeic acid oligomers, yunnaneic acids A and B are formally dimeric and heterodimeric adducts of yunnaneic acids C and D. Herein we report the first total syntheses of yunnaneic acids C and D featuring the formation of their bicyclo[2.2.2]octene cores in a single step from simple precursors via an oxidative dearomatization/ Diels-Alder cascade that may have biogenetic relevance. In addition, exploitation of the key intermediate resulting from this cascade reaction has enabled rapid access to the structurally related caffeic acid metabolite rufescenolide through an unexpected Lewis acid-mediated reduction. Finally, we report the results of extensive model studies toward forming the dimeric yunnaneic acids A and B. These explorations indicate that the innate reactivities of the monomeric fragments do not favor spontaneous formation of the desired dimeric linkages. Consequently, enzymatic involvement may be required for the biosynthesis of these more complex family members.
机译：从云南丹参的根中分离出来的云南酸A-D是咖啡酸的六聚体（A和B）和三聚体（C和D）组装体，具有一系列具有合成挑战性和结构趣味性的结构域。 being酸A和B除了是咖啡酸低聚物外，还是酸C和D的形式二聚体和杂二聚体加合物。在此，我们报道featuring酸C和D的第一批总合成，其特征是它们的双环形成[2.2.2]通过简单的前体通过氧化脱芳香化作用/狄尔斯-阿尔德级联反应从一个简单的前体中分离出辛烯核，它们可能具有生物遗传相关性。另外，对由该级联反应产生的关键中间体的利用，使得能够通过意想不到的路易斯酸介导的还原来快速获得与结构相关的咖啡酸代谢物rufescenolide。最后，我们报告了广泛的模型研究结果，以形成二聚的壬二酸A和B。这些探索表明，单体片段的先天反应性不利于所需二聚键的自发形成。因此，这些更复杂的家庭成员的生物合成可能需要酶的参与。

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