We report the first collective biomimetic synthesis of xanchryones A (1), B (2), and I-N (3-8, respectively), all featuring a benzoxazole scaffold, by employing a synthetic strategy based on biogenetic building blocks (BBBs). These compounds were efficiently assembled in six steps from commercially available 3,4,5-trimethoxyphenol. Notably, the benzoxazole ring was constructed for the first time using rationally designed p-quinones and amino acids as substrates, enabling precise control of the nitrogen and oxygen positions in the benzoxazole ring. This BBB-based biomimetic strategy provides a concise route to structurally diverse natural benzoxazoles and offers insight into their biogenetic origin.
Shen et al. (Thu,) studied this question.