Molecular diversity from naphthalene nucleus

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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.