A convenient method for the synthesis of indoles has
been developed
by the sequential orchestration of the cross-coupling reaction of o-haloaniline and PIFA oxidation of the resulting 2-alkenylanilines.
A highlight of this two-step indole synthesis is a modular strategy
which is applicable to both acyclic and cyclic starting materials.
Particularly noteworthy is the regiochemistry that is complementary
to the Fischer indole synthesis and related variants. Direct preparation
of N–H indoles with no N-protecting
group is also advantageous.
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 IIB is among the most interesting antibiotics in this family, it presents numerous problems related to its chemical structure, such as instability at most pH levels, weak solubility in water, and resistance by bacteria. As a response to the need for developing new antimicrobial agents, we have designed a new analog of pristinamycin IIB, 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 IIB. Our multistep synthetic approach relies on few key reactions, namely a Wittig reaction, a Grubbs reaction, and dihydroxy, -difluoro API (Advanced Pharmaceutical Intermediate) synthesis
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