Triquinane based natural products via cycloadditions and metathesis

Abstract

Triquinane natural products are an interesting class of polycyclic frameworks that have attracted considerable interest because of their distinct structures and diverse array of biological applications such as antibacterial, antifungal, and anticancer properties and biological diversity of these scaffolds make them promising candidates for drug discovery and medicinal chemistry. These frameworks have a central structure of bicyclo[2.2.1]heptane ring which is linked to another cycloalkane ring generating the a unique tricyclic arrangement. The design and synthesis of triquinane framework is very challenging because of their intricate three-dimensional structure and the requirement for accurate organization of numerous stereocenters. Based on thorough review of literature, cycloadditions and metathesis play a pivotal role for constructing these exciting class of complex frameworks in an efficient and selective manner. In this review we focused mainly on how cycloadditions and metathesis strategies are significant in total synthesis of these interesting class of scaffolds. Here, we summarized the synthetic strategies of linear, angular, and propellane types of triquinane natural products via different cycloaddition protocols as well as photothermal and olefin metathesis which are used as key steps in the total synthesis.