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首页> 外文学位 >Towards the Total Synthesis of the Xiamycin Family of Indolosesquiterpenes: Synthesis Of Oridamycins A and B.
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Towards the Total Synthesis of the Xiamycin Family of Indolosesquiterpenes: Synthesis Of Oridamycins A and B.

机译：迈入吲哚倍半萜的夏霉素家族的全合成：奥立霉素A和B的合成。

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摘要

The xiamycin family of indolosesquiterpenes comprises bioactive compounds isolated from several strains of Streptomyces. Several dimeric family members have shown strong activity against several strains of bacteria, including methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin resistant Enterococcus (VRE). These promising initial results, coupled with the limited production of these compounds from their natural sources, prompted the design of a unified synthetic strategy capable of producing several family members from a common synthetic intermediate.;Structurally, the xiamycin family members consist of a carbazole fused to a trans-decalin ring system. The difference between xiamycin A and oridamycin A is a single epimeric stereocenter at C16. It was envisioned that a key oxidative radical cyclization could produce both stereochemical patterns---with free-radical conditions generating the stereochemistry associated with oridamycin A, and chelated radical conditions producing the stereochemistry corresponding to xiamycin A.;The total synthesis of oridamycins A and B was completed, utilizing a free-radical cyclization that correctly set three contiguous stereocenters, including two quaternary carbons. The fused carbazole was produced using a 6?-electrocyclization/aromatization sequence. Finally, oridamycin B was accessed through a palladium-catalyzed, oxime-directed C-H oxidation.
机译：吲哚倍半萜的厦霉素家族包含从数种链霉菌菌株中分离的生物活性化合物。几个二聚体家族成员已显示出对多种菌株的强大活性，包括耐甲氧西林的金黄色葡萄球菌（MRSA）和耐万古霉素的肠球菌（VRE）。这些有希望的初步结果，加上这些化合物天然来源的生产量有限，促使设计出一种统一的合成策略，该策略能够从一种常见的合成中间体中生产多个家族成员。结构上，厦霉素家族成员是由稠合的咔唑组成的。反式十氢化萘环系统。 xiamycin A和oridamycin A之间的区别是C16处有一个单向异构立体中心。可以预见，一个关键的氧化自由基环化反应既可以产生立体化学模式-自由基条件产生与奥利霉素A相关的立体化学，又可以与螯合的自由基条件产生对应于烟霉素A的立体化学；奥利霉素A和B是通过自由基环化完成的，该环化正确设置了三个连续的立体中心，包括两个季碳。使用6′-电环化/芳族化序列产生稠合的咔唑。最后，通过钯催化的肟定向的C-H氧化获得了奥里达霉素B。

著录项

  • 作者

    Trotta, Adam Howell.;

  • 作者单位

    Weill Medical College of Cornell University.;

  • 授予单位 Weill Medical College of Cornell University.;
  • 学科 Organic chemistry.;Chemistry.
  • 学位 Ph.D.
  • 年度 2018
  • 页码 312 p.
  • 总页数 312
  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类
  • 关键词

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