BYU

Abstract by Tanner Brinley

Personal Infomation


Presenter's Name

Tanner Brinley

Degree Level

Undergraduate

Abstract Infomation


Department

Chemistry and Biochemistry

Faculty Advisor

Merritt Andrus

Title

Pyrroloindoline synthesis

Abstract

Pyrroloindolines made by Reisman’s synthesis have shown anti-cancer characteristics and are made through the 3+2 cycloaddition of 2-amidoacrylate and an indole, via a chiral ligand for stereoselectivity. This method however gives low yield and limited stereoselectivity. Our overall goal is to create multiple pyrroloindoline products using our 3+2 cycloaddition reaction. These products can be used in a variety of healthcare capacities including cancer and disease treatment. We have proposed two pathways to create a pyrroloindoline through 3+2 cycloaddition of N-methyl-3-methyl indole and acyloxazolidinone. 1) using a chiral auxiliary. 2) mirroring the Reisman reaction using a chiral ligand and an achiral oxazolidinone. We hypothesize that acyloxazolidinone with a chiral auxiliary group will create stereoselective reactions which will stop a mixture of enantiomers from forming during the 3+2 cycloaddition. We believe the benzyl group hinders the approach of the substrate on one face giving us only diastereomers and easier separation.