Improved screening of small molecules
Our ChemSci Pick of the Week demonstrates a more efficient way to turn hydrocarbon feedstock compounds into valuable fine chemicals. This could be used for the synthesis of a variety of natural products or pharmaceutically relevant compounds, and help overcome a drug discovery bottleneck.
The industrial production of 1,3-Dienes happens on a mammoth scale. For example, 1,3-butadiene and isoprene – commonly used in rubber manufacture – are produced in the order of 13 million and 0.8 million tons per year, respectively. Efficient catalytic conversion of hydrocarbon-based feedstocks, rather than more traditional routes, can make chemical processes ‘greener’, reduce costs and prevent waste.
In this week’s Chemical Science pick, a team of researchers from Technische Universität Berlin in Germany describe the difunctionalisation – modification by the introduction of two functional groups – of these chemicals in one step, with an ability to tune the reaction to selectivity generate the desired product configuration.
"For this work, we developed a three-component coupling reaction of 1,3-dienes (isoprene and its derivatives), a diboron reagent, and ketones: and converted these substrates to value-added chiral tertiary homoallylic alcohols," said corresponding author Martin Oestreich. "These serve as common building blocks for the synthesis of a variety of natural products and pharmaceutically relevant compounds."
In particular, this holds the potential to help overcome a drug discovery bottleneck related to screening small molecules, due to their ability to bind to a preselected protein target. This increases the efficiency and reduces the overall cost of preparing new small molecules with a particular configuration.
Oestreich said: "If a molecule contains two asymmetric centres, there are up to four possible stereoisomers. Different stereoisomers – while very closely related chemically – can have vastly different properties. For example, one could be a medicinally useful drug while the other could cause harm in the human body.
"Lack of efficient access to collections of synthetic compounds that display stereochemical diversity is a key bottleneck in the small-molecule [drug] discovery process. In this work, we realize the controlled formation of the two possible diastereomers, each in highly enantioenriched form, from a common set of precursors by employing different ligands."
This article is free to read in our open access, flagship journal Chemical Science: Jian‐Jun Feng, Yan Xu et al., Chem. Sci., 2019, Advance Article. DOI: 10.1039/ C9SC03531A. You can access our 2019 ChemSci Picks in this article collection.
ChemSci Pick of the Week
Chemical Science is the flagship journal of the Royal Society of Chemistry and publishes findings of exceptional significance from across the chemical sciences. It is a global journal for the discovery and reporting of breakthroughs in basic chemical research, communicated to a worldwide audience without barriers, through open access. All article publication charges have been waived, meaning that the journal is free to read and free to publish.
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