In an interview, Uttam Tambar with Chemical Today Magazine talks about his research on streamlining the synthesis of pharmaceutical drugs by making internal alkenes.
Tambar is an associate professor at the W. W. Caruth, Jr. Scholar in Biomedical Research, The University of Texas Southwestern Medical Center at Dallas.
Research insight on speedy drug development.
For many years, chemists have sought to develop new reactions to the direct conversion of inexpensive feedstock hydrocarbons into valuable materials such as pharmaceuticals. However, internal alkenes, which are one of the most abundant classes of hydrocarbons, contain many carbon-hydrogen bonds. The selective transformation of one carbon-hydrogen bond into a new bond is a significant challenge, resulting in difficult to separate mixtures of compounds. If the goal is to synthesize a pharmaceutical drug from a hydrocarbon starting material, the indiscriminate transformation of multiple carbon-hydrogen bond would render the chemical process useless, because we would generate potentially dangerous side products in addition to the desired product.
Our group has developed a method for the direct conversion of a variety of double bond-containing internal alkenes into multifunctional intermediates through the implementation of a chiral catalyst and a unique oxidant. These multifunctional compounds, which are obtained in high purity, are readily transformed into an assortment of molecules that will streamline the synthesis of future pharmaceutical drugs.
New chemical reaction that accelerates drug development.
Our group has developed a new reaction that selectively oxidizes internal alkenes. The products of this reaction are useful building blocks that can accelerate the drug development process.
Applications of these molecules.
We are now able to use internal alkenes as substrates for enantioselective allylic oxidation. Alkenes, in general, are ideal starting points for drug production, because they are inexpensive and abundant. Internal alkenes, in particular, are the most common class of alkenes found among organic substrates. But historically they have also been the most challenging class of unsaturated hydrocarbons to be used as substrates for enantioselective allylic oxidation.
Insight into chiral catalyst used in the research.
In our research, we utilize an antimony-BINOL complex as the chiral catalyst. Pioneered by Corey and co-workers, the complexation of SbCl5 and BINOL results in the formation of a Lewis acid assisted Brønsted acid, in which the protons of BINOL are rendered more acidic due to coordination with SbCl5. In our system, we believe the oxidant is activated by the SbCl5-BINOL complex through a LUMO lowering effect.
Read more: Finding a new way of drug development
In an interview, Uttam Tambar with Chemical Today Magazine talks about his research on streamlining the synthesis of pharmaceutical drugs by making internal alkenes.
Tambar is an associate professor at the W. W. Caruth, Jr. Scholar in Biomedical Research, The University of Texas Southwestern Medical Center at Dallas.
Research insight on speedy drug development.
For many years, chemists have sought to develop new reactions to the direct conversion of inexpensive feedstock hydrocarbons into valuable materials such as pharmaceuticals. However, internal alkenes, which are one of the most abundant classes of hydrocarbons, contain many carbon-hydrogen bonds. The selective transformation of one carbon-hydrogen bond into a new bond is a significant challenge, resulting in difficult to separate mixtures of compounds. If the goal is to synthesize a pharmaceutical drug from a hydrocarbon starting material, the indiscriminate transformation of multiple carbon-hydrogen bond would render the chemical process useless, because we would generate potentially dangerous side products in addition to the desired product.
Our group has developed a method for the direct conversion of a variety of double bond-containing internal alkenes into multifunctional intermediates through the implementation of a chiral catalyst and a unique oxidant. These multifunctional compounds, which are obtained in high purity, are readily transformed into an assortment of molecules that will streamline the synthesis of future pharmaceutical drugs.
New chemical reaction that accelerates drug development.
Our group has developed a new reaction that selectively oxidizes internal alkenes. The products of this reaction are useful building blocks that can accelerate the drug development process.
Applications of these molecules.
We are now able to use internal alkenes as substrates for enantioselective allylic oxidation. Alkenes, in general, are ideal starting points for drug production, because they are inexpensive and abundant. Internal alkenes, in particular, are the most common class of alkenes found among organic substrates. But historically they have also been the most challenging class of unsaturated hydrocarbons to be used as substrates for enantioselective allylic oxidation.
Insight into chiral catalyst used in the research.
In our research, we utilize an antimony-BINOL complex as the chiral catalyst. Pioneered by Corey and co-workers, the complexation of SbCl5 and BINOL results in the formation of a Lewis acid assisted Brønsted acid, in which the protons of BINOL are rendered more acidic due to coordination with SbCl5. In our system, we believe the oxidant is activated by the SbCl5-BINOL complex through a LUMO lowering effect.
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