Graduate School of Life Sciences, Tohoku University, 2-1-1 Katahira, Aoba-ku, Sendai 980-8577 (Japan).
Angew Chem Int Ed Engl. 2015 Jan 12;54(3):868-73. doi: 10.1002/anie.201409629. Epub 2014 Nov 12.
(-)-Lyngbyaloside B is a 14-membered macrolide glycoside isolated from the marine cyanobacterium Lyngbya sp. as a cytotoxic substance by Moore and co-workers. The first total synthesis of (-)-lyngbyaloside B and the reassignment of its stereostructure is described. The synthesis features an Abiko-Masamune aldol reaction, a vinylogous Mukaiyama aldol reaction, and a macrocyclization involving an acyl ketene intermediate for the construction of the macrocyclic backbone, which contains an acylated tertiary alcohol. The antiproliferative activity of selected compounds against a small panel of human cancer cell lines is also reported.
(-)-Lyngbyaloside B 是一种 14 元大环糖脂，由 Moore 及其同事从海洋蓝藻 Lyngbya sp. 中分离得到，具有细胞毒性。本文描述了 (-)-lyngbyaloside B 的首次全合成和其立体结构的重新确定。该合成方法的特点是采用了 Abiko-Masamune 醛醇反应、乙烯基 Mukaiyama 醛醇反应以及涉及酰基烯酮中间体的大环化反应，构建了包含酰化叔醇的大环骨架。此外，还报道了选定化合物对一小部分人类癌细胞系的抗增殖活性。
