New Strategies for the Synthesis of Carbocyclic and Heterocyclic Compounds

有机合成计划正在资助 Rick L博士的研究项目。丹海瑟 丹海瑟博士 他将继续卓有成效地开发新方法， 合成碳环和杂环化合物，其包含 五元环。 这将提供所需的新工具 随着工业要求的日益复杂， 农业 该项目的一个重要目标是持续发展 最近发现的将军<$3 +2！环化战略 在此过程中，丙二烯基硅烷作为三碳 环化单元与亲电子π键结合以形成 新的五元环 将这一战略扩展到 几类重要的五元环的合成 将研究环化合物。 的具体目标 感兴趣包括环戊酮衍生物和杂环 系统，如吡咯和碳青霉烯。 研究也将 目的是制定一项全面的综合报告 取代的甘菊环。 甘菊环是最好的 已知种类的多环非苯型芳族化合物，和 最近，新的电子性质和生物学性质 某些天然的和半合成的甘菊环的活性 导致了这些化合物在商业上的重要应用 在医学和电子照相等领域。 然而，在这方面， 这些领域的进展受到了阻碍， 在合成甘菊环的非常少的通用方法中， 特别是替代系统。 一个将军的发展 三加二！取代的甘菊环的成环路线将提供 获得具有潜在药物应用的化合物， 液晶元件和新型电子材料。 该项目的另一个重要目标是发展 新的环化方法的基础上异常容易周环 和丙二烯的阴离子闭环反应。 初步 已经进行的实验表明，某些 丙二烯衍生物在室温下进行有效的环化反应。 非常温和的条件。 该项目的主要目标 将这一过程应用于一种新的合成， 取代的吲哚。 吲哚核是 大量天然产物结构特征 包括植物生长调节剂和临床重要的 大药厂 相对较少的通用方法， 取代吲哚的结构存在，并且新的 将研究的方法将提供更好的机会， 各种重要的吲哚衍生物。

The Organic Synthesis Program is funding the continuation of the research program of Dr. Rick L. Danheiser. Dr. Danheiser will continue his fruitful development of new methods to synthesize carbocyclic and heterocyclic compounds containing five-membered rings. This will provide the new tools required by the increasingly complex requirements of industry and agriculture. One important aim of the project is the continued development of the recently discovered general ı3+2! annulation strategy. In this process an allenylsilane functions as a three-carbon annulation unit combining with an electrophilic pi bond to form a new five-membered ring. The extension of this strategy to the synthesis of several important classes of five-membered ring compounds will be investigated. Specific targets of interest include cyclopentanone derivatives and heterocyclic systems such as pyrroles and carbapenems. Research will also be carried out aimed at the development of a general synthesis of substituted azulenes. The azulenes constitute the best known class of polycyclic nonbenzenoid aromatic compounds, and recently the novel electronic properties and biological activity of certain natural and semi-synthetic azulenes have led to commercially important applications of these compounds in fields such as medicine and electrophotography. However, progress in these areas has been hindered by the availability of very few general methods for the synthesis of azulenes, particularly substituted systems. The development of a general ı3+2! annulation route to substituted azulenes will provide access to compounds with potential applications as drugs, liquid crystal elements, and novel electronic materials. Another important objective of the project is the development of new cyclization methods based on unusually facile pericyclic and anionic ring closure reactions of allenes. Preliminary experiments have been carried out that indicate that certain allene derivatives undergo efficient cyclization under remarkably mild conditions. A principal aim of the project will be the application of this process in a new synthesis of substituted indoles. The indole nucleus is the central structural feature in a large array of natural products including plant growth regulators and clinically important pharmaceuticals. Relatively few general methods for the construction of substituted indoles exist, and the new methodology to be investigated will provide improved access to a variety of important indole derivatives.