Highly Convergent and Stereoselective Synthesis of Heterodimeric Polycyclic Alkaloids

With this award, the Chemical Synthesis Program of the Chemistry Division is funding Professor Mohammad Movassaghi of the Department of Chemistry at the Massachusetts Institute of Technology to explore and develop new general methodology for the formation of challenging C-C bonds by directed radical combination reactions. This project focuses on the development of mild conditions for synthesis of diazenes as intermediates in guided advanced fragment assembly. An integral part of the study will focus on evaluating and broadening the chemistry of these intermediates in chemical synthesis. The proposed study includes a thorough development of our preliminary results supported by additional mechanistic probes and studies that will provide important insight into the stereochemical course of these diazene-based assemblies for preparation of complex heterodimeric polycyclic alkaloids.

Such chemistry will provide precedence of a general strategy in controlled complex chemical synthesis that will have broad impact in pharmaceutical, agricultural, and fine-chemical industries where designed complex molecules are used in biological and chemical research endeavors. The broader impacts involve training graduate students and postdoctoral researchers, broadening participation through the inclusion of undergraduate and visiting student researchers on the project, and continued contribution by the research group to MIT's Chemistry Outreach Program at local high schools.