International Research Experience for Undergraduates

Sophie Klein

2002 Participant


Synthesis of Cyathins

The goal of the research is to synthesize a tryciclic ketone. This ketone will be used to synthesize a cyathin molecule. Representative cyathins, as scabronines and erinacines, are chemicals inducers of nerve growth factor (NGF), a small peptide which is an important factor for growth, development and maintenance of the central and peripheral nervous system. The NGF should be injected directly in the nervous system, so an easy way is to have inducers of the NGF.

Klein Diagram

The first step is to synthesize the starting reactants for the tricyclic ketone (1) by using classical organic chemistry. The next step is to synthesize the ketone by a cuprate addition. Then, we do an anodic oxidation by electrochemistry. We use differents enones as the cyclohex-2-enone, the 3-methylcyclohex-2-enone,the 2-methyl-cyclopent-2-enone or the 3-methyl-cyclopent-2-enone. The next step would be a [4+3] cycloaddition to obtain the cyathin core, a basic skeleton for the scabronine and erinacine.