Site-selective C-H functionalization of (hetero)arenes bearing amine (NR2) or alkoxy (OR) groups offers exciting potential for constructing molecular complexity. This review summarizes various para-C-H functionalization reactions driven by native functional groups through electronic guidance. We have critically evaluated reaction designs, highlighting the challenges and providing a mechanistic rationale. We hope this review will serve as a valuable guide for future developments in this field.

Indole-based diterpenoids are a specific class of naturally occurring bioactive molecules that have garnered significant interest from synthetic organic chemists. These compounds exhibit diverse and fascinating biological activities, including anticancer, antifungal, and anti-inflammatory properties. Moreover, the molecular architectures of these indole-based diterpenoids are highly complex, presenting significant synthetic challenges. This complexity, combined with their biological relevance, makes them ideal targets for total synthesis. In this review, we focus on anominine, an indole-based diterpenoid, and summarize recent advances in its total synthesis. Anominine is notable for its biological activity and serves as the parent compound for several other congeners isolated from the fungal sclerotia of the genus Aspergillus. Spp. Various research groups have developed diverse synthetic routes to access anominine. By highlighting those notable syntheses, we aim to showcase the progress in this area and provide insights into future directions for the synthesis of related natural products.