In the broad area of Organic Chemistry, the main focus of Prof. Gharpure’s research has been the development of new synthetic methods, which would be applicable for the synthesis of natural and unnatural products of biological relevance.
We have used vinylogous functional groups, namely vinylogous carbonate and carbamate, in the stereoselective synthesis of oxa- and aza-cycles. The reactivity of vinylogous carbonates/carbamates was studied under a variety of conditions. Thus, our group has used radical cyclisation to vinylogous carbonates/carbamates for the stereoselective synthesis of new oxa-cages as well as angular oxa- and aza-triquinanes. An efficient strategy for the synthesis of tetrahydrofurans (THFs), tetrahydropyrans (THPs) and oxepane derivatives has been developed employing a tandem SN2-Michael addition to vinylogous carbonates.
On the other hand, intramolecular cyclopropanation of vinylogous carbonates/carbamates using carbenes led to the oxygen and nitrogen bearing donor-acceptor substituted cyclopropanes (DACs). These DACs could be converted into diversely functionalized THFs, THPs, lactones, pyrrolidine, piperidine and lactam derivatives. Vinylogous carbonates/carbamates were also found to give useful reactions in the presence of Lewis acids undergoing intramolecular Pictet-Spengler as well as Prins type cyclizations.
Vinylogous Carbonate/Carbamate Cyclization · Radical Cyclisation Strategy
Apart from using vinylogous functional groups in the synthesis of oxa- and aza-cycles, our group has developed efficient strategies for the synthesis of flavans and isoflavans. Flavans and isoflavans are class of compounds which are thought to be responsible for biological activity of traditional Chinese medicines. The strategy relying on o-quinone methides has been used for the total synthesis of variety of natural products of this family like equol, 3′-hydroxyequol, vestitol and myristinins.
Flavan / Isoflavan Scaffold · o-Quinone Methide Strategy
Equol, 3′-Hydroxyequol, Vestitol and Myristinins Synthesis
Chelonin A & C Total Synthesis · Stereoselective Strategy
Very recently, we have also developed stereoselective strategies for construction of morpholines and oxazepenes, which are important pharmacophores. This method has also been used for the total synthesis of chelonin A and Chelonin C.
The lab continues to push boundaries in catalysis, organometallic chemistry, and asymmetric synthesis — developing scalable and green methods applicable to pharmaceutical and agrochemical industries.
Phone: 022 2576 7171
Email:
sjgharpure@chem.iitb.ac.in
Address:
3rd floor main, Room #440-A
Department of Chemistry
IIT Bombay, Powai
Mumbai 400076, India
OSL · Department of Chemistry · IIT Bombay
