Allied studies on total sythesis of cyclic tripeptide TMC-95 via an iridium catalyzed borylation/deborylation strategy and teaching organic chemistry in "words"

Arylboronate esters are versatile synthetic building blocks. Iridium catalyzed C-H activation/borylation reactions are a green way of making such building blocks as these reactions often obviate the need for prior functionalization (e.g. halogenation), the use of pyrophoric reagents, cryogenic conditions, etc. Installation of multiple boron substituents about the starting arene and then Ir catalyzed selective deborylation of the individual borons can allow for the formation of an even greater diversity of borylated building blocks.The regioselectivity of Ir-catalyzed borylation is usually driven by sterics, however heterocycles are known to borylated at positions that exhibit heightened C-H acidity through the influence of the heteroatom. The regioselective borylation attained with a tryptophan derivative has been utilized in the development of a novel convergent route to the TMC-95 core. While pursuing a model synthesis of this natural product, the ability of bismuth salts to catalyze deborylations was discovered. These bismuth salts mediated methods can be highly selective in the in the deborylation of di and triborylated indoles. Furthermore, bismuths compounds are safe and less expensive as compared to the Ir-catalysts that facilitated deborylation. Numerous screening experiments on both substrates and other metal salts afforded a better understanding of how these novel deborylations can be applied in various synthetic settings and provided insight into possible mechanisms.Also, while I was a teaching assistant and a fixed-term instructor during my graduate studies at Michigan State University, I gradually realized that teaching is my passion and I am prepared to start my independent career and be an independent thinking teacher for the organic chemistry area.Owing to the nature of the subject, organic chemistry can be very visually distracting, and the image can be overpowering during student's learning. Like it or not students will try memorization first, our hypothesis is that once they know the "organic transformation formula" in words, via memorization or any other method, then introducing them to the structures of these functional groups will come with added context, and once they make that jump from word to structure they will be in a better position to understand reaction mechanisms. More importantly, understanding those reaction mechanisms will enable the student to progress to more complex topics.By introducing functional group transformations without the "clutter" of structures, we predict that once structures are introduced students will prioritize what's important because they will have trained their minds to ask what is the functional group, not "where did I see that structure in my notes".In short, we aim to train students to focus their attention on the reactive functional group of an organic molecule by emphasizing the use of WORDS to describe functional group transformation and teach the organic chemistry as the second language.