Pd-catalyzed synthesis of substituted heteroaromatic fluoranthene analogues and studies towards the total synthesis of truncatone C and imeluteine

Abstract

Fluoranthenes represent an important class of polycyclic aromatic compounds with important applications in modern chemistry and materials science. In addition to being present in the structural core of a variety of fungal natural products, fluoranthenes have also been widely employed as fluorescent probes and in organic electronics. Despite the recent advances in this area, the chemistry of heteroaromatic fluoranthene analogues, in other words, acenaphthylenes fused with heteroaromatic rings such as pyridine, furan, benzofuran, pyrazole, etc. has remained largely unexplored. In this work, we have synthesized a variety of heteroaromatic fluoranthene analogues via a Pd-catalyzed tandem Suzuki-Miyaura and C-H arylation reaction sequence with using different types of boronic acids and esters. Natural products have an undeniable importance in pharmaceutical chemistry, and for the development of new medicinal drugs, natural products and their derivatives still provide significant contribution. In this project, the total synthesis of natural products truncatone C and imeluteine is targeted.