Abstract by Braden Kartchner
Chemistry and Biochemistry
Optimization of Synthesis of Antiviral F4-4
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.