An Extraordinary Photochemical Reaction of Pyrrole - A New Tool for Molecular Complexity

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This proposal aims to explore a powerful photochemical reaction recently discovered in our laboratory. A variety of N-butenyl substituted pyrroles have been found to undergo an extraordinary photocycloaddition/rearrangement sequence to give tricyclic fused aziridines of high molecular complexity. Early studies have shown that as long as the pyrrole bears an electron withdrawing group on the 2-position the reaction sequence is highly tolerant of substitution. We will investigate the scope of the cycloaddition reaction by examining the effects of side chain substitution with a variety of cyclic and acyclic alkenes. The resulting aziridines will themselves be reactive species and should undergo a number of useful bond forming ring opening reactions. Once developed and understood the methodology will be applied as the key step in a very short synthesis of the alkaloid dendrobine. Overall the work in this proposal should serve to highlight the value of photochemistry and photochemical technology in modern chemical synthesis.