The synthesis of natural product-inspired oxygen heterocycles has long been hindered by the development of enantioselective methods for forming important cores, such as chromane and xanthone cores. Through the investigation of enantioselective methods for the synthesis of tetrahydroxanthones, a method was developed using copper bisoxazoline catalysis. This method utilized [4+2] cycloaddition to set two stereocenters at once, one of which is a quaternary carbon. This product can be further derivatized to an intermediate of morphine and provides opportunity for the synthesis of natural product-inspired chromane and xanthone cores. The tolerance of this method shows its amenability to a structure activity relationship study. This reaction mechanism was investigated using a Linear Free Energy Relationship Study. Hammett plots revealed that a positive charge was built up during the reaction which agreed with our proposed mechanism. However, it appeared that when a more substituted ligand was used, the more sterically demanding environment decreased the effect of the electronic properties of the substrate on the reaction.

• This report represents the work of one or more WPI undergraduate students submitted to the faculty as evidence of completion of a degree requirement. WPI routinely publishes these reports on its website without editorial or peer review.

Creator

• Noel, Julia R.

Publisher

• Worcester Polytechnic Institute

Identifier

• 16956
• E-project-040521-093736

Advisor

• Mattson, Anita Elaine

Year

• 2021

Sponsor

• National Institute of Health
• Worcester Polytechnic Institute

Date created

• 2021-04-05

Resource type

• Major Qualifying Project

Major

• Chemistry

Rights statement

• In Copyright