A new direction of synthetic chemistry was developed in the Institute of Bioorganic Chemistry RAS
Small molecules play a critical role in many biological processes and are used as drugs and other research tools.
As a result of joint work carried out by the Laboratory of bioinformatics approaches in combinatorial chemistry and biology and a group of heterocyclic compounds with a support of Laboratory of biomolecular NMR-spectroscopy, a novel unique method for the synthesis of spirocyclic derivatives based on the use of a new class of cyclopropanes was developed. The results of the study are published in the Organic Letters journal.
Spiroannulated cyclopropanes, which incorporate imidazol-5-one fragment, were examined in the reaction with aldehydes to form tetrahydrofuran cycle. The studied compounds could be regarded as a new variant of donor-acceptor cyclopropanes – popular in the organic synthesis recent building-blocks, which function as 1,3-zwitterionic synthons.
Spiro[imidazol-5-one-tetrahydrofurans], which are the products of the reaction, constitute as seminal alpha-amino acid derivatives. A spirocyclic structure makes them advantageous objects for drug design.