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首页> 外文学位 >Multicomponent reactions in organic synthesis: An approach to viridin and viridin analogs.
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Multicomponent reactions in organic synthesis: An approach to viridin and viridin analogs.

机译：有机合成中的多组分反应：一种制备viridin和viridin类似物的方法。

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摘要

The use of the Passerini (3CC) and Ugi (4CC) reactions to construct novel analogs of the viridin family of furanosteroids and the synthesis of monomers for use in ring opening metathesis polymerization (ROMP) reactions was examined.; A strategy for the synthesis of viridin and wortmannin analogs was investigated that would maintain a high degree of synthetic flexibility while allowing for quick and efficient synthesis of a large number of analogs. The synthesis of highly functionalized oxabicyclo[2.2.1]heptadiene derivatives through the sequential use of an Ugi or Passerini multi-component coupling reaction was examined. The multicomponent reaction allowed for the quick assembly of a large number of structurally diverse products that were subjected to an intramolecular acetylene/furan Diels-Alder reaction. This tandem reaction provided derivatives that can be further functionalized to give analogs of potent PI-3K inhibitors viridin and wortmannin.; The combined application of multicomponent coupling reactions and olefin metathesis chemistry for the preparation of new chemical entities with application as novel biomaterials was also investigated. The compatibility of these two complexity-building reactions made them ideal for the use in generation of novel monomer and polymeric structures. The peptide-like functionality of the resulting monomers may allow for metal binding with application as metal scavenging agents or macromolecular ligands for asymmetric synthesis.
机译：检验了Passerini（3CC）和Ugi（4CC）反应用于构建呋喃类固醇的viridin家族的新类似物以及用于开环复分解聚合（ROMP）反应的单体合成的方法。研究了一种合成viridin和渥曼青霉素类似物的策略，该策略将保持高度的合成灵活性，同时允许快速高效地合成大量类似物。研究了通过顺序使用Ugi或Passerini多组分偶联反应合成高度官能化的氧双环[2.2.1]庚二烯衍生物。多组分反应允许快速组装大量经受分子内乙炔/呋喃Diels-Alder反应的结构多样的产物。该串联反应提供了可以进一步官能化以产生有效PI-3K抑制剂viridin和渥曼青霉素的类似物的衍生物。还研究了多组分偶联反应和烯烃复分解化学在制备新的化学实体中的结合应用，并将其作为新型生物材料。这两个复杂性增强反应的相容性使其非常适合用于生成新型单体和聚合物结构。所得单体的类似肽的官能团可允许金属结合并用作金属清除剂或用于不对称合成的大分子配体。

著录项

  • 作者

    Robotham, Claude Vincent.;

  • 作者单位

    University of Florida.;

  • 授予单位 University of Florida.;
  • 学科 Chemistry Organic.
  • 学位 Ph.D.
  • 年度 2003
  • 页码 146 p.
  • 总页数 146
  • 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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