Small cyclic peptides have attracted attention for decades since they have shown high potentials in drug discovery material science and catalysis research.  Head-to-tail condensation between the N- and C- termini of the corresponding linear peptides represents the most straightforward synthesis for cyclic peptides as widely described in the literature. However, lactamization reactions to form tetrapeptides usually require harsh conditions which can cause partial epimerization, side reactions and low yields.  As part of our ongoing research program dedicated to the development of innovative and efficient cyclization procedures, we now report a novel, straightforward, efficient and mild approach to the preparation of 6-membered cyclic dipeptides and 14-membered cyclic tetrapeptides via a solution phase using benzotriazole auxiliary. Our method has shown advantages over literature methods with regard to reaction efficiency, atom economy and stereoflexibility.

Benzotriazole mediated gateway to 6-membered dipeptides and 14-membered tetrapeptides via intra- and inter-molecular lactamizations

245th National Meeting (2013)

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