Zhang Hui, Feng Jiaxuan, Wang Di, Tang Bencan, Xu Chao, Ye Tao
State Key Laboratory of Chemical Oncogenomics, Peking University Shenzhen Graduate School, Shenzhen 518055, China.
Department of Chemical and Environmental Engineering, Faculty of Science and Engineering, The University of Nottingham Ningbo China, Ningbo 315100, China.
Molecules. 2025 Apr 3;30(7):1597. doi: 10.3390/molecules30071597.
Alternapyrone, a bioactive polyketide produced by the fungal host , is biosynthesized by a polyketide synthase encoded by the gene cluster. Despite its known bioactivity, the stereochemical configuration of the three stereogenic centers in its polyketide backbone has remained unresolved. In this study, we determined the complete stereostructure of alternapyrone using an integrative approach that combines predictive, rule-based stereochemical analysis with experimental validation through total synthesis. The efficient total synthesis enabled the precise assignment of the hypothesized stereochemistry by matching the synthetic product to the natural compound. This comprehensive study conclusively established the absolute configuration of alternapyrone.
交替吡喃酮是由真菌宿主产生的一种生物活性聚酮化合物，由基因簇编码的聚酮合酶生物合成。尽管其具有已知的生物活性，但其聚酮骨架中三个手性中心的立体化学构型仍未确定。在本研究中，我们采用了一种综合方法来确定交替吡喃酮的完整立体结构，该方法将基于规则的预测性立体化学分析与通过全合成进行的实验验证相结合。高效的全合成通过将合成产物与天然化合物匹配，实现了对假设立体化学的精确归属。这项全面的研究最终确定了交替吡喃酮的绝对构型。
