• 主题
高级搜索  >
历史搜索 清空历史
首页> 外文学位 >Development of new synthetic methodology and enantioselective synthesis of the A-B-C ring system of the Veratrum alkaloids.
【24h】

Development of new synthetic methodology and enantioselective synthesis of the A-B-C ring system of the Veratrum alkaloids.

机译：藜芦生物碱的A-B-C环系统的新合成方法的开发和对映选择性合成。

获取原文
获取原文并翻译 | 示例
页面导航
  • 摘要
  • 著录项
  • 相似文献
  • 相关主题

摘要

This work is divided into four chapters spanning three projects. The first two projects involve new synthetic methodology and the third uses synthetic protocols developed in our lab towards the total synthesis of a natural product.;The first project describes the practical synthesis of a geometrically defined diiodo compound for use in organic synthesis. Most allylic iodides are subject to decomposition and are difficult to handle. An improved method for purification and isolation is described. Several derivatives were also prepared to display the synthetic utility of the diiodide.;A new route to enantiomerically pure alpha-amino acids is described in the second chapter. This route is based on esterification of the carboxylic acid with L-menthol, followed by diazo transfer and NH insertion into o-anisidine. This protocol allows for either enantiomer of the amino acid to be produced. The intermediates in the synthetic route can be monitored for diastereomeric purity by 1H-NMR.;The final chapter describes a new route to the 6-6-5 system of the Veratrum alkaloids using an approach developed in our lab. A two step process of asymmetric allylation followed by an oxy-Cope rearrangement gave rise to an enantiomerically pure alpha,beta-dialkyl ketone. A Robinson annulation was then used to form the 6-6 bicyclic system. A rhodium catalyzed CH insertion was employed to construct the third ring. A model route for the endgame of the synthesis of (-)-veratramine was also developed.
机译：这项工作分为四个章节，涵盖三个项目。前两个项目涉及新的合成方法，第三个项目使用我们实验室针对天然产物的全合成开发的合成方案。;第一个项目描述了用于有机合成的几何定义的二碘代化合物的实际合成。大多数烯丙基碘化物易于分解且难以处理。描述了一种纯化和分离的改进方法。还制备了几种衍生物以显示二碘化物的合成效用。第二章描述了一种对映体纯的α-氨基酸的新途径。该途径基于羧酸与L-薄荷醇的酯化，然后重氮转移和NH插入邻茴香胺中。该方案允许产生氨基酸的任一对映异构体。合成途径中的中间体可以通过1H-NMR监测非对映异构体的纯度。最后一章介绍了使用我们实验室开发的方法制备藜芦生物碱的6-6-5系统的新途径。经过不对称烯丙基化的两步过程，然后进行氧基-Cope重排，生成对映体纯的α，β-二烷基酮。然后使用鲁滨逊环空法形成6-6双环系统。铑催化的CH插入被用来构建第三个环。还开发了合成（-）-verrrramine的终局模型路径。

著录项

  • 作者

    Berry, James F.;

  • 作者单位

    University of Delaware.;

  • 授予单位 University of Delaware.;
  • 学科 Chemistry Organic.
  • 学位 Ph.D.
  • 年度 2010
  • 页码 95 p.
  • 总页数 95
  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类
  • 关键词

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