TOWARD THE SYNTHESIS OF A TRIFLUORINATED PRISTINAMICIN II_B ANALOG AS NOVEL ANTIBIOTIC

Streptogramins are potent antibiotics against numerous highly resistant pathogens and therefore are used in last-resort human therapy. These antibiotics are formed of both A and B group compounds named Pristinamycins that differ in their basic primary structures.

Although Pristinamycin II_B is among the most interesting antibiotics in such a family, it presents numerous problems related to its chemical structure such as instability to most pHs, weak solubility in water, and resistance by bacteria.

As a response to the need of developing new antimicrobial agents, we have designed a new analog of Pristinamycin II_B, based most importantly on the introduction of fluorine atoms. We conjectured indeed that the introduced modifications may solve the above-mentioned problems exhibited by Pristinamycin II_B.

Our multistep synthetic approach relies on few key reactions, namely a Wittig reaction, a Grubbs reaction, and a dihydroxy, -difluoro API (Advanced Pharmaceutical Intermediate) synthesis.