News & Events

When

Date - March 13, 2019
1:00 pm - 2:00 pm

What

CHE 751 Literature Seminar
Faculty Advisor: Dr. Kimberly Petersen
Talk Title: The Biomimetic Approach to the Synthesis of Flavonoids

Abstract:

Flavonoids are a naturally derived compounds with diverse biological activity. One class of flavonoid compounds contains a 2,8-dioxabicyclo[3.3.1]nonane or a 2,4-diarylbenzopyran skeleton at its core. To produce these core structures, the proposed biosynthetic pathway involves an annulation or an oxidative cyclization, utilizing a benzopyrlium salt and a phenolic compound. Synthetic efforts have been made to develop a bio-inspired flavonoid synthesis, to mimic the proposed biosynthetic pathway. Herein, this talk will focus on synthetic methodology implemented to synthesize core structures 2,8-dioxabicyclo[3.3.1]nonane and 2,4-diarylbenzopyran derivatives. The latter part of this talk will focus on the biomimetic strategy developed by Yang and co-workers, to insert a stereocenter into the core structure of the flavonoid compounds synthesized.¹ Yang and colleagues were able to achieve this by developing a stereoselective addition to a planar cationic electrophile, via Chiral Anion Phase Transfer (CAPT) catalysis.