Catalytic Asymmetric Synthesis of Complex Multi-functional and Bioactive Molecules via Cascade Reactions of Curcumins
Implementing Organization
Indian Institute Of Technology Bombay
Principal Investigator
Prof. Irishi Narayanan Namboothiri
Indian Institute Of Technology Bombay
irishi@iitb.ac.in
CO-Principal Investigator
Prof. Samir K Maji
Indian Institute Of Technology Bombay, Iit Po Powai,Maharashtra,Mumbai-400076
Project Overview
Development of novel organocatalytic asymmetric cascade reactions for the synthesis of complex multi-functional and bioactive molecules using curcumin and its non-natural analogues as the key substrates is proposed here. The new methodologies will focus primarily on the poorly explored and challenging Michael donor-acceptor reactivity of curcumins. Various cinchona and amino acid derived bifunctional catalysts bearing at least one Broensted base (e.g. tertiary amine) and one Broensted acid (e.g. thiourea and squaramide) moiety will be employed in these reactions. The cascade (one-pot multi-step) reactions are expected to generate complex fused and spiro molecular scaffolds with multiple chiral centers and functional groups with high degree of selectivities and effect kinetic resolution of racemic substrates. The different levels of selectivities (chemo, regio, diastereo and enantio) will be controlled with appropriate choice of substrates, reagents/catalysts and conditions. Besides the final product in each scheme, the stable intermediate after each step will be isolated and characterized to enrich the scope and diversity of the compounds that can be synthesized by our approach and screened for their biological properties against neurodegenerative diseases such as Parkinson’s, Alzheimer’s and dementia.