ChemComm Milestones – Showkat Rashid

We are excited to share the success of Showkat Rashid’s first-time independent article in ChemComm; “Chemoselective oxidation of aromatic aldehydes to carboxylic acids: potassium tert-butoxide as an anomalous source of oxygen included in the full milestones collection. 

Read our interview with Showkat below.

What are the main areas of research in your lab and what motivated you to take this direction?

Our lab is primarily focused on the synthesis of bioactive natural products having therapeutic potential against diseases like Alzheimer’s disease and AMR. Additionally, scalable synthesis of drugs/drug-like molecules, and the development of novel methodologies for building complexities are also pursued in our lab. During my high school days, I got the opportunity to watch some chemical reactions carried out by our science teacher which was highly fascinating to me. The impact of that exposure at the school level was so deep and I used to make crude soap from cooking oil and caustic soda at home. This interest in chemical reactions remained throughout my academic journey and motivated me to be an organic chemist.

Can you set this article in a wider context?

Carboxylic acids and their derivatives like esters, amides, and anhydrides represent quintessential building blocks for pharmaceutical, agrochemical, and polymer industries. The main chemical transformation to access carboxylic acids is the oxidation of corresponding aldehydes and these oxidations have been primarily implemented using stoichiometric amounts of various metal-based oxidants. Considering their serious toxicity issues, nascent H2O2 oxidations,
organocatalytic oxidations, and NHC-based oxidations have also emerged. Despite their promise, these methods suffer several limitations in terms of high catalyst loading, longer reaction times, limited substrate scope, and operational complexities.

Most of these reported methods utilize diverse primary or secondary oxidants (as oxygen sources) and proceed through Criegee intermediate which is difficult to handle, especially at an industrial scale. Any oxidation strategy that averts such an intermediate is highly desired. In this context, we have disclosed an unprecedented potassium tert-butoxide-mediated oxidation protocol for the conversion of aromatic/heteroaromatic aldehydes to their corresponding carboxylic acids. Interestingly, this method uses KOtBu as an oxygen source, and can easily oxidize a range of aldehydes to carboxylic acids under ambient conditions. The extraordinary chemoselectivity displayed by this method to oxidize a relatively less preferred functional group in the presence of more oxidation-prone functional group/s highlights the advantage of this protocol over the methods reported so far. Operational simplicity, fast reaction kinetics, fair substrate scope, and gram-scale operations are some of the highlights of this method.

What do you hope your lab can achieve in the coming year?

In the coming year, we are committed to exploring novel strategies for assembling complex natural products and drug-like molecules. New reactions involving a high level of selectivity and economy will be our prime focus.

Describe your journey to becoming an independent researcher.

Formally my research career started with the M. Phil degree enrolled at the University of Kashmir-Srinagar and I was fortunate enough to have worked with Dr. Bilal A. Bhat at the CSIR-IIIM Srinagar. My initial training was in medicinal chemistry and, exploration of plant-derived bioactive compounds against cancer. Subsequently, I joined Dr. Bhat for my doctoral studies and worked on a collaborative research project between Dr. Bhat and Prof. Goverdhan Mehta in the area of Natural product synthesis at the University of Hyderabad. During this time, I got trained in multistep synthesis and eventually completed the total synthesis of several complex bioactive natural/non-natural compounds. After completing my doctoral studies in 2019, I did my initial postdoctoral training with Prof. Mehta at the University of Hyderabad, and later in 2020 moved to Prof. Shinichi Saito’s research group at Tokyo University of Science-Japan, wherein my research was oriented toward the design and synthesis of rotaxane based molecular machines. My journey to an independent researcher began in 2022 when I joined the Natural Product and Medicinal Chemistry Division (NPMCD) of IIIM Jammu as a senior scientist and my present research interests are centered on the synthesis of bioactive natural products of medicinal importance and development of new organic transformations.

What is the best piece of advice you have ever been given?

Both of my Ph.D. supervisors, Dr. Bhat and Prof. Mehta trained me to be more realistic in life. Their advice used to be “There is no free lunch in life” and “It is always better to have one bird in the hand than two in the bush”.

Why did you choose to publish in ChemComm?

I believe that ChemComm is one of the highly reputed chemistry journals with a wide readership across all the disciplines of chemical science. In addition to being a competitive platform for novel and application-oriented research findings, the highly systematic and robust nature in terms of publishing these ideas are some of the factors that attracted me to publish in ChemComm.

  Dr. Showkat Rashid is currently working as a senior scientist at CSIR-Indian Institute of Integrative Medicine (IIIM) Jammu-India. He pursued his Bachelor of Science, Master of Science, and M.Phil. in chemistry from the University of Kashmir, Srinagar. Subsequently, he joined Dr. Bilal A. Bhat (Principal Scientist, IIIM-Srinagar) for his Ph.D. program and worked under a collaborative research project between Dr. Bhat and Prof. Goverdhan Mehta in the area of Natural product synthesis. His doctoral research encompassed diverse areas of contemporary interest in synthetic organic and medicinal chemistry.
After completing his doctoral studies in 2019, Dr. Showkat did his initial postdoctoral training with Prof. Goverdhan Mehta at the University of Hyderabad, with a prime focus on the synthesis of complex bioactive natural products and molecules of human imagination. Later on, in 2020 he moved to Prof. Shinichi Saito’s research group at Tokyo University of Science-Japan, wherein his research was oriented towards the design and synthesis of molecular machines. These studies eventually led to the synthesis of novel fluorenone-based [2]-rotaxanes with potential applications as smart drug delivery systems. While in Japan, Dr. Showkat was awarded the prestigious start-up research grant by the Japan Society for the Promotion of Science (JSPS), Japan for the year 2022-2023.
At CSIR-IIIM Jammu, Dr. Showkat’s research interests are tuned towards the total synthesis of bioactive natural products/drugs, new methods for building complexity, and multistep synthesis of biologically privileged scaffolds having the potential to combat Alzheimer’s disease and antimicrobial resistance.

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