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首页> 外文学位 >Application of the Bradsher cycloaddition for the syntheses of naproxen and sakyomicin A and glycosidation via glycals and phenyl(bisphenylthio)sulfonium salts: Effect of the glycal structure on the face selectivity.
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Application of the Bradsher cycloaddition for the syntheses of naproxen and sakyomicin A and glycosidation via glycals and phenyl(bisphenylthio)sulfonium salts: Effect of the glycal structure on the face selectivity.

机译：Bradsher环加成在萘普生和沙曲霉素A的合成中的应用以及通过糖基和苯基（双苯硫基）ulf盐进行糖基化的方法：糖基结构对面部选择性的影响。

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摘要

Part 1. Attempts are made for the syntheses of bioactive compounds naproxen and sakyomicin A using the Bradsher cycloaddition as the key reaction. Naproxen, a non-steroidal antiinflammatory compound, has a 6-methyoxy-naphthalene moiety with a chiral substituent at its C-2. The required alkyl chain is appended to the naphthalene nucleus using the Bradsher reaction between a vinyl ether bearing the chiral alkyl chain and an isoquinolinium salt.; The ABC-ring analog of sakyomicin A, an angucycline antibiotic, is the other target. The key reaction in the proposed synthesis of this target molecule is an intramolecular version of the Bradsher reaction, which requires a 3-substituted-4-alkoxy-isoquinoline. The precursors for the chiral alkyl side chain and the 4-alkoxy-isoquinoline are synthesized and an attempt is made to couple them so as to obtain the desired 3-substituted-4-alkoxy isoquinoline.; Part 2. Glycosyl transfer via glycals, activated by phenyl(bisphenylthio)sulfonium salts to a variety of nucleophiles is studied. The method shows preferential {dollar}beta{dollar} selectivity leading to 2-phenylthio substituted 2-deoxy-{dollar}beta{dollar}-glycosides. A series of glycals are examined in order to determine the effect of their structure on the glycosidation stereochemistry. The face selectivity is strongly influenced by the substituents on the glycal. Glycals with rather rigid structures also give {dollar}beta{dollar}-glycosides as the major products. The allylic 3-pseudoequatorial and 4-equatorial substituents have little contribution in the stereochemical outcome of the reaction while allylic 3-pseudoaxial and 4-axail substituents act as major directors.; This glycosidation method is applied to the synthesis of 1-O-phenyl-2-deoxy-{dollar}beta{dollar}-D-fucopyranoside, the AA{dollar}spprime{dollar}-ring analog of aureolic acid.
机译：第1部分。尝试使用Bradsher环加成作为关键反应合成生物活性化合物萘普生和沙曲霉素A。萘普生，一种非甾体类抗炎化合物，具有一个6-甲氧基萘部分​​，其C-2处带有一个手性取代基。使用带有手性烷基链的乙烯基醚和异喹啉鎓盐之间的Bradsher反应将所需的烷基链附加到萘核上。另一目标是抗细菌性沙金霉素A（一种环霉素​​抗生素）的ABC环类似物。该靶分子的拟议合成中的关键反应是Bradsher反应的分子内形式，该反应需要3-取代的4-烷氧基-异喹啉。合成了手性烷基侧链和4-烷氧基-异喹啉的前体，并试图将它们偶合以获得所需的3-取代的-4-烷氧基-异喹啉。第二部分。研究了通过苯基（双苯硫基）ulf盐活化的糖基将糖基转移到各种亲核试剂上的过程。该方法显示出优先的{beta}β{dollar}选择性，导致2-苯硫基取代的2-deoxy- {dollar}β{dollar}-糖苷。检查了一系列糖基，以确定它们的结构对糖基化立体化学的影响。面部选择性受到糖基上取代基的强烈影响。具有相当刚性的结构的乙二醇也产生{dolal}β{dollar}-糖苷作为主要产物。烯丙基的3-伪赤道和4-赤道取代基对反应的立体化学结果几乎没有贡献，而烯丙基的3-伪轴和4-甲氧基取代基起主要作用。这种糖苷化方法被用于合成1-O-苯基-2-脱氧-{β} {{}}-D-呋喃核糖苷，即金黄色酸的AA {sp}} {{}}环类似物。

著录项

  • 作者

    Grewal, Gurmit.;

  • 作者单位

    City University of New York.;

  • 授予单位 City University of New York.;
  • 学科 Chemistry Organic.
  • 学位 Ph.D.
  • 年度 1991
  • 页码 207 p.
  • 总页数 207
  • 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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