Synthesis of Heterocyclic Natural Products

在有机和大分子化学项目的支持下，宾夕法尼亚州立大学化学系的Steven M. Weinreb教授正在进行几种具有生物学意义的复杂天然分子的立体选择性全合成，并辅以新的和实用的有机合成方法的发展。一种肝毒性生物碱柱精子素的全合成方法使用了Weinreb教授的n -亚砜基二酚Diels-Alder方法。本文还将合成几种结构独特的多环海洋苔藓虫生物碱。新分离的新型五环吲哚生物碱tronocarpine的全合成将利用1-羟基吲哚的独特化学性质。将研究新的化学合成方法，包括一种简单的替代Eschenmoser偶联反应制备葡萄酰胺和氨基甲酸酯，以及使用n -亚砜基化合物作为形成糖苷和n -糖苷键的试剂。构建通常具有理想生物或药物活性的复杂分子需要开发新的和复杂的有机分子合成方法。随着新方法的发展，它们最终必须通过应用于实际的综合问题来测试和证明是有效的。这样的测试还提供了思维过程和有机合成实践方面的培训，这对将成为下一代有机化学家的学生的教育发展至关重要。在有机和大分子化学项目的支持下，宾夕法尼亚州立大学化学系的Steven M. Weinreb教授正在探索有机合成的新实用方法的发展，并将其应用于几种具有生物学意义的复杂自然发生分子的全合成。

With the support of the Organic and Macromolecular Chemistry Program, Professor Steven M. Weinreb, of the Department of Chemistry at Pennsylvania State University, University Park, is carrying out the stereoselective total synthesis of several complex naturally-occurring molecules of biological significance, complemented by the development of new and practical methods for organic synthesis. An approach to the total synthesis of the hepatotoxic alkaloid cylindrospermopsin uses as a pivotal step Professor Weinreb's N-sulfinyl dienophile Diels-Alder methodology. Several structurally unique polycyclic marine bryozoan alkaloids of the chartelline/securamine class will also be synthesized. The total synthesis of the recently isolated novel pentacyclic indole alkaloid tronocarpine will utilize the unique chemistry of 1-hydroxyindoles. New methods of chemical synthesis will be investigated, including a simple alternative to the Eschenmoser coupling reaction for preparing vinylogous amides and carbamates, and the use of N-sulfinyl compounds as reagents for the formation of glycosidic and N-glycosidic bonds.Construction of the often-complex molecules which display desirable biological or pharmaceutical activity requires the development of new and sophisticated methods for the synthesis of organic molecules. As new methods are developed, they ultimately must be tested and proven effective through their application to real synthetic problems. Such testing also provides training in the thought processes and practice of organic synthesis, vital to the educational development of students who will become the next generation of practicing organic chemists. With the support of the Organic and Macromolecular Chemistry Program, Professor Steven M. Weinreb, of the Department of Chemistry at Pennsylvania State University, University Park, is exploring the development of new and practical methods for organic synthesis and applying them to the total synthesis of several complex naturally-occurring molecules of biological significance.