Department of Chemistry, Brock University, 1812 Sir Isaac Brock Way, St. Catharines, ON L2S 3A1, Canada.
Department of Chemistry and Biochemistry, Texas State University, San Marcos, TX 78666, USA.
Molecules. 2022 Jun 14;27(12):3809. doi: 10.3390/molecules27123809.
A 15-step chemoenzymatic total synthesis of C-1 methoxycarbonyl narciclasine () was accomplished. The synthesis began with the toluene dioxygenase-mediated dihydroxylation of -dibromobenzene to provide the corresponding -dihydrodiol () as a single enantiomer. Further key steps included a nitroso Diels-Alder reaction and an intramolecular Heck cyclization. The C-1 homolog was tested and evaluated for antiproliferative activity against natural narciclasine () as the positive control. Experimental and spectral data are reported for all novel compounds.
完成了 C-1 甲氧基羰基纳曲林 () 的 15 步酶促全合成。该合成从甲苯双加氧酶介导的 -二溴苯的二羟基化开始，以提供相应的 -二羟基化合物 () 作为单一对映体。进一步的关键步骤包括亚硝酮 Diels-Alder 反应和分子内 Heck 环化。对 C-1 同系物 进行了测试，并评估了其对天然纳曲林 () 的抗增殖活性作为阳性对照。所有新化合物都报告了实验和光谱数据。
