Synthetic explorations of the briarane jungle: progress in developing a synthetic route to a common family of diterpenoid natural products

Abstract

The briarane diterpenoids are a large family of marine natural products that have been primarily isolated from gorgonian octocorals around the world. Structurally, the family is characterized by a trans -fused bicyclo[8.4.0]tetradecane ring system containing a central, stereogenic, all-carbon quaternary carbon (C1) flanked by three additional stereocentres (C2, C10, C14). Many family members have demonstrated biological activity in numerous areas, including: cytotoxicity, anti-inflammatory, antiviral, antifungal, immunomodulatory and insect control. Despite their interesting structural properties and bioactivity, the briaranes have been largely overlooked by the synthetic community. However, in recent years, several research groups have reported progress toward developing a synthetic route to these natural products. Most of these efforts have focused on the stereoselective construction of the central C1–C2–C10–C14 stereotetrad. This review will discuss the various synthetic efforts aimed at the briarane diterpenoids along with the challenges that remain.