Development of synthetic organic chemistry methods to selectively transform steroid derivatives to access known metabolites and impurities, and novel drug-like structures

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Dalton Pharma Services is a leading manufacturer of pharmaceutical products and provider of analytical services to the pharmaceutical and biotechnological industries. Dalton is particularly interested in steroid compounds because of the high demand for standards, metabolites, and impurities from customers for their research and development needs. They are currently facing a technological problem in efficiently making certain classes of steroid compounds.This collaborative project between Dalton Pharma and Prof. Marc J. Adler's lab at Ryerson University seeks to discover new chemical methods to selectively transform molecules of biological interest, including steroids. The specific goal is to develop highly specific ways to reduce ketones to secondary alcohols, allowing for the differentiation of two ketones in a steroid molecules with similar reactivity profiles; this selective reactivity is vital to make particular subsets of steroid analogues. Currently differentiation requires a multi-step synthetic process, resulting in significant chemical waste, expenditure of time, and decrease in product yield. We aim to directly differentiate the two functional groups for chemical transformation, thus providing a more efficient and greener path to the desired products. Such products include known metabolites of and impurities in drugs. This method will also provide ready access to new bioactive molecules to be evaluated as potential probes or therapeutics. The collaborative project will train two Master's students who will develop innovative and industrially relevant chemical synthesis methods in close collaboration with Dalton Pharma scientists.