Department of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba 305-8571, Japan.
J Nat Prod. 2022 Aug 26;85(8):2082-2089. doi: 10.1021/acs.jnatprod.2c00476. Epub 2022 Jul 14.
New bromoditerpenes having an α-methylene carbonyl structure, azuriaplysins A () and B (), were isolated from the sea hare . Their relative stereostructures were determined based on one- and two-dimensional NMR spectroscopic analysis. In addition, the absolute stereostructures were determined by the total synthesis of both enantiomers of azuriaplysins A () and B (), the key points of which were bromocyclization of farnesol and optical resolution of a key intermediate. Azuriaplysin B () and its enantiomer exhibited moderate cytotoxicity against HeLa S3 cells.
新型具有α-亚甲基羰基结构的溴二萜，来自海螺的天青杀素 A()和 B()，被分离出来。其相对立体结构是基于一维和二维 NMR 光谱分析确定的。此外，通过天青杀素 A()和 B()的对映体的全合成，也确定了其绝对立体结构，其中的关键步骤是法呢醇的溴环化和关键中间体的光学拆分。天青杀素 B()及其对映异构体对 HeLa S3 细胞表现出中等的细胞毒性。
