...
首页> 外文期刊>Nature Communications >Total synthesis and antiviral activity of indolosesquiterpenoids from the xiamycin and oridamycin families
【24h】

Total synthesis and antiviral activity of indolosesquiterpenoids from the xiamycin and oridamycin families

机译:厦霉素和奥达霉素家族的吲哚倍半萜类化合物的总合成和抗病毒活性

获取原文
           

摘要

Indolosesquiterpenoids are a growing class of natural products that exhibit a wide range of biological activities. Here, we report the total syntheses of xiamycin A and oridamycins A and B, indolosesquiterpenoids isolated from Streptomyces . Two parallel strategies were exploited to forge the carbazole core: 6π-electrocyclization/aromatization and indole C2–H bond activation/Heck annulation. The construction of their trans -decalin motifs relied on two diastereochemically complementary radical cyclization reactions mediated by Ti(III) and Mn(III), respectively. The C23 hydroxyl of oridamycin B was introduced by an sp3 C–H bond oxidation at a late stage. On the basis of the chemistry developed, the dimeric congener dixiamycin C has been synthesized for the first time. Evaluation of the antiviral activity of these compounds revealed that xiamycin A is a potent agent against herpes simplex virus–1 (HSV-1) in vitro .
机译:吲哚倍半萜类化合物是一类不断增长的天然产物,具有广泛的生物活性。在这里,我们报告了从链霉菌中分离得到的厦霉素A,奥达霉素A和B,吲哚倍半萜类化合物的总合成。开发了两个平行的策略来锻造咔唑核:6π-电环化/芳香化和吲哚C2-H键活化/ Heck环化。它们的反式十氢萘基序的构建分别依赖于由Ti(III)和Mn(III)介导的两个非对映化学互补的自由基环化反应。奥达霉素B的C23羟基是在后期通过sp 3 C–H键氧化引入的。在发展起来的化学基础上,首次合成了二聚体同源物双氧霉素C。对这些化合物的抗病毒活性进行评估后发现,厦霉素A在体外可有效抵抗单纯疱疹病毒-1(HSV-1)。

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