Abstract by Jared Neeley
Chemistry and Biochemistry
Production of Pyrroloindolines through 3+2 Cycloaddition reactions
Pyrroloindolines are an important class of molecules that exhibit important biological activity. One example is (+)- Physostigmine, a cholinesterase inhibitor currently used to treat glaucoma, Alzheimer’s disease, myasthenia gravis, delayed gastric emptying, and orthostatic hypotension. In 2010 Reisman successfully synthesized a pyrroloindoline through the 3+2 cycloaddition of an indole and 2- amidoacrylate, utilizing a chiral ligand in order to allow for stereoselectivity. While this mechanism can produce a pyrroloindoline, it does so with lower yields and less stereoselectivity than we believe possible. We propose a novel chiral auxiliary-based mechanism to synthesize the pyrroloindoline structure, using a chiral auxiliary to ensure enantioselectivity and higher yields and with more versatility. Our hypothesis is that a chiral auxiliary group on acyloxazolidinone will allow for stereoselective reactions, allowing us to select for specific diastereomers when performing a 3+2 cycloaddition to produce pyrroloindolines.