Pyridine Synthesis via an Olefin C-H Alkenylation/Azaelectrocyclization Strategy

描述（由申请人提供）：由于这种结构基序在天然产物和生物活性化合物中普遍存在，因此开发含氮杂环的简明立体选择性合成方法是一个活跃的研究领域。吡啶基序（及其饱和变体）在具有重要生物学意义的化合物中尤其广泛存在，因此其立体选择性制备方法在文献中有很好的代表性。本研究计划的具体目的是概述一种利用金属催化烯烃C- H键烯化/氮杂电环化序列立体选择性制备此类杂环的新方法。这种策略允许简洁的立体选择性合成吡啶，提供从现成的起始材料快速获得这类重要的化合物。多取代吡啶，手性饱和吡啶和独特的融合双环吡啶系统都很容易使用这种新策略。本文还概述了该方法在生物活性偶氮糖(-)-苦马豆素全合成中的应用。开发在实验室中简明制备治疗药物的新方法仍然是一个活跃的研究领域。本研究旨在开发这些新方法，并将其应用于具有潜在治疗价值的药物的制备。

DESCRIPTION (provided by applicant): The development of methodology for the concise stereoselective synthesis of nitrogen-containing heterocycles is an active area of research, owing to the prevalence of such structural motifs in natural products and bioactive compounds. The pyridine motif (and saturated variants thereof) is in particular widely represented in compounds of biological importance, and consequently methods for its stereoselective preparation are well represented in the literature. It is the specific aim of this research proposal to outline a new method for the stereoselective preparation of such heterocycles employing a metal catalyzed olefinic C- H bond alkenylation/azaelectrocyclization sequence. This strategy allows for the concise stereoselective synthesis of pyridines, providing rapid access to this important class of compounds from readily available starting materials. Polysubstituted pyridines, chiral saturated pyridines, and uniquely fused bicyclic pyridine systems are all readily accessible using this new strategy. The application of this methodology to the total synthesis of the bioactive aza sugar (-)-swainsonine is also outlined. The development of new methods to concisely prepare therapeutic drugs in the laboratory continues to be an active area of research. This research aims to develop such new methods, and to apply them toward the preparation of drugs of potential therapeutic value.