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首页> 外文学位 >A unified strategy toward the biogenetically related oroidin derived bisguanidine marine alkaloids: Palau'amines, styloguanidines and axinellamines.
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A unified strategy toward the biogenetically related oroidin derived bisguanidine marine alkaloids: Palau'amines, styloguanidines and axinellamines.

机译：生物素相关的麦草碱衍生双胍海洋生物碱的统一策略：帕劳胺，苯乙烯基胍和乙酰内酰胺。

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摘要

Natural products that exhibit potent biological activity in conjunction with novel structural features constitute attractive synthetic targets. The oroidin-derived class of bisguanidine marine alkaloids including palau'amine (i), styloguanidine (iv) and their brominated congeners as well as the axinellamines (vii–x) share a complex polycyclic framework that features a densely functionalized cyclopentane core coupled with potent biological activity, which most notably include immunosuppressive, chitinase inhibitory and antibacterial activity, respectively.*; The overreaching goal of this research project was directed toward the development of a general and concise synthetic strategy, which would grant access to the spirocyclic core of this class of biogenetically related natural products. In this regard, our synthetic strategy was inspired by a biosynthetic proposal for palau'amine, featuring a Diels-Alder reaction and chlorination/ring contraction sequence as key synthetic transformations. The successful implementation of this strategy delivered the fully functionalized cyclopentane moiety embedded in spirohydantoin core xi. The intermolecular mode of chlorination furnished a spirohydantoin, which is epimeric at C5 relative to C17 in palau'amine and epimeric at C3 relative to C11 in axinellamine.*; *Please refer to dissertation for diagrams.
机译：天然产物表现出强大的生物活性以及新颖的结构特征，构成了诱人的合成靶标。来源于鸟苷的双胍海洋生物碱类，包括帕劳胺（ i ），苯乙烯基胍（ iv ）及其溴化同类物以及阿奇胺（viel– x ）共享一个复杂的多环框架，该框架的特征是具有高密度功能化的环戊烷核心，并具有强大的生物活性，其中最显着的分别包括免疫抑制，几丁质酶抑制和抗菌活性。该研究项目的首要目标是开发一种通用且简洁的合成策略，该策略将使此类生物遗传相关天然产物的螺环核心具有可及性。在这方面，我们的合成策略是受生物合成的关于帕劳胺的提议启发，该方案以Diels-Alder反应和氯化/环收缩序列为关键合成转化为特征。该策略的成功实施将完全功能化的环戊烷部分包埋在螺乙内酰脲核心 xi 中。氯化的分子间模式提供了螺乙内酰脲，它在palau'amine中相对于C17在C5处是异构体，而在乙酰氨基胺中相对于C11在C3处是差向异构体。 *请参考论文的图表。

著录项

  • 作者

    Dilley, Anja Susanne Hazle.;

  • 作者单位

    Texas A&M University.;

  • 授予单位 Texas A&M University.;
  • 学科 Chemistry Organic.
  • 学位 Ph.D.
  • 年度 2003
  • 页码 274 p.
  • 总页数 274
  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类 有机化学;
  • 关键词

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