Electrophilic Selenocyclofunctionalization in the Synthesis of Biologically Relevant Molecules

Abstract

The cyclofunctionalization reactions promoted by electrophilic selenium species are undoubtedly very powerful methodologies in organic chemistry for the construction of different oxygen- and nitrogen-containing heterocycles. If alkene is bearing suitably oriented internal nucleophile, such as OH, COOH, NHR, a variety of heterocyclic compounds, such as ethers, lactones, pyrolidines, piperidines can be synthesized by the usage of this extremely useful synthetic protocol. In the last decade great progress had been done in the field of selenium promoted ring closure reactions by the means of selectivity, efficiency in asymmetric synthesis and simplicity of the procedure. Vast variety of heterocyclic products that can be prepared by this method, combined with its other advantages, has inspired its utilization in some total synthesis of naturally occurring compounds which have nitrogen or oxygen heterocycles as scaffolds in their structures. Our review is focused on broad possibilities of electrophilic selenocyclofunctionalization protocol as decisive and important stage in the total synthesis of biologically important molecules. Keywords: Organoselenium reagents, cyclization, total synthesis, bioactive compounds, oxygen heterocycles, nitrogen heterocycles.