Collective Biomimetic Synthesis of Benzoxazole Xanchryones A, B, and I-N Based on Biogenetic Building Blocks
Qin-Cheng Shen1,2,3, Guan-Qiu Qin1,2,3, Wen-Hua Yu1,2,3
1State Key Laboratory of Bioactive Molecules and Druggability Assessment, Guangdong Basic Research Center of Excellence for Natural Bioactive Molecules and Discovery of Innovative Drugs, Jinan University, Guangzhou 510632, People's Republic of China.
Abstract:
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.
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