University of Novi Sad, Faculty of Sciences, Department of Chemistry, Biochemistry and Environmental Protection, Trg Dositeja Obradovića 3, 21000 Novi Sad, Serbia.
University of Novi Sad, Faculty of Sciences, Department of Chemistry, Biochemistry and Environmental Protection, Trg Dositeja Obradovića 3, 21000 Novi Sad, Serbia.
Bioorg Chem. 2022 Nov;128:106073. doi: 10.1016/j.bioorg.2022.106073. Epub 2022 Aug 3.
Development of a synthetic route applicable to d-ribose and d-xylose enabled the synthesis of cleistanolate putative structure, its five stereoisomers, and led to revision and confirmation of absolute stereochemistry of the natural product. Key steps of the synthesis included zinc-mediated THF ring-opening and stereoselective dihydroxylation under the Upjohn conditions. The first total synthesis of cleistanolate was completed in eight steps starting from d-xylose. The C-5 stereocenter of the natural product was assigned the correct (5S)-stereochemistry. Cytotoxicity of natural product was briefly investigated.
开发了一条适用于 D-核糖和 D-木糖的合成路线，实现了 cleistanolate 假定结构、其五个立体异构体的合成，并对天然产物的绝对立体化学进行了修正和确认。合成的关键步骤包括锌介导的 THF 开环和在 Upjohn 条件下的立体选择性二羟基化。从 D-木糖出发，经过八步完成了 cleistanolate 的首次全合成。天然产物的 C-5 立体中心被赋予了正确的（5S）立体化学构型。天然产物的细胞毒性也进行了简要研究。
