BYU

Abstract by Braden Kartchner

Personal Infomation


Presenter's Name

Braden Kartchner

Degree Level

Undergraduate

Abstract Infomation


Department

Chemistry and Biochemistry

Faculty Advisor

Merritt Andrus

Title

Optimization of Synthesis of Antiviral F4-4

Abstract

Synthesis of antiviral natural product F4-4 requires the use of a novel intramolecular styryl alkynyl Diels-Alder (ISDA) reaction. The precursor steps leading up to the ISDA are functional but require further optimization for yield and purity. Two sub-products, labeled A and B, are joined together to make an ester product that then is subjected to the ISDA. We optimized the purity of product B via recrystallization in hexanes instead of flash chromatography. We explored the key esterification reaction of A and B using a variety of synthetic techniques, such as the Mitsunobu reaction and Ghosez esterification. We are still further optimizing this reaction for higher yield and purity, using an acyl chloride as our reagent to form the ester. We have monitored this reaction via TLC and its unique reaction conditions present a challenge in the total synthesis of F4-4.