Molecular diversity from naphthalene nucleus

应用有机化学的所有方面都依赖于产生各种具有有趣性质的新颖分子结构的能力。这对合成有机化学家提出了持久的要求，要求他们开发和微调各种程序，使之能够合成所需的结构框架。申请人的研究实验室在过去几年中一直积极参与由萘核合成新型分子骨架的工作。在这一不断发展的专业知识的基础上，申请人计划继续设计实用的合成路线，以构建一系列具有各种分子拓扑和官能团的重要的新型分子骨架。这些假定的合成设计将导致合成一系列准甾体和新型的以萘为基础的恶环，此外还将为重要的有机转化开发几种实用的合成方法。不对称合成将通过催化手性诱导进行。为这项研究选择的特定目标骨架预计具有广泛的拓扑和性质。只要有可能，就会进行研究，以揭示所合成的分子的任何有趣的光谱和电子性质。还将努力使合成化合物的库可供具有互补专业知识的同行科学家使用，以研究它们作为制药、催化剂、光笼、荧光团等的潜力。在这笔赠款的任期内，约8名研究生和约20名高级本科生将接受有机合成艺术和科学写作以及其他研究相关技能的高质量培训。除了传授HQP强化培训外，这一努力还将导致在方法学开发领域，特别是在准类固醇和邻甲基萘醌的产生和应用领域，获得新的知识。致力于开发准类固醇药物(最终是人类健康)的药物化学界将从拟议的研究结果中受益。

All aspects of applied organic chemistry rely on the ability to generate a vast variety of novel molecular architectures with interesting properties. This places a persistent demand on the synthetic organic chemists to develop and fine-tune various procedures that enable the synthesis of the desired structural frameworks. The research laboratory of the applicant has actively been involved in the synthesis of novel molecular frameworks from naphthalene nucleus over the past several years. Building on this evolving expertise, the applicant plans to continue devising practical synthetic routes to construct an array of important novel molecular frameworks, from naphthalene core, having a variety of molecular topology and functional groups. The putative synthetic designs will lead to synthesis of a selection of quasi-steroids and novel naphthalene-based oxacycles in addition to the development of several practical synthetic methodologies for important organic transformations. Asymmetric synthesis will be undertaken employing chiral induction through catalysis. The specific target skeletons selected for this investigation are expected to possess a wide variety of topologies and properties. Wherever possible studies will be undertaken to unravel any interesting spectroscopic and electronic properties of the molecules synthesized. Attempts will also be made to make the library of compounds synthesized available to fellow scientists with complementary expertise to study their potential as pharmaceuticals, catalysts, photocages, fluorophores, etc. During the tenure of this grant, ~8 graduate students and ~20 advanced undergraduate students will receive high quality training in the art of organic synthesis and scientific writing among other research related skills. In addition to imparting intensive HQP training, this endeavor will lead to new knowledge in the field of methodology development in general and in the area of quasi-steroid and o-naphthoquinone methide generation and application in particular. The medicinal chemistry community working on the development of quasi-steroidal drugs (and ultimately human health) will benefit from the outcome of the proposed research.