Total Synthesis, Stereochemical Reassignment, and Biological Evaluation of (-)-Lyngbyaloside B
Total Synthesis, Stereochemical Reassignment, and Biological Evaluation of (-)-Lyngbyaloside B
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DOI：
10.1002/anie.201409629
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发表时间：
2015-01-12
影响因子：
16.6
通讯作者：
Sasaki, Makoto
中科院分区：
文献类型：
--
作者：
Fuwa, Haruhiko;Okuaki, Yuta;Sasaki, Makoto
（-）-Lyngbyaloside B是摩尔及其同事从海洋蓝细菌Lyngbya sp.中分离的14元大环内酯糖苷，作为细胞毒性物质。首次全合成了（-）-lyngbyaloside B，并对其立体结构进行了重排。该合成的特征在于Abiko-Masamune羟醛缩合反应、乙烯基化Mukaiyama羟醛缩合反应和涉及用于构建大环骨架的酰基烯酮中间体的大环化，所述大环骨架包含酰化叔醇。还报道了所选化合物对一小组人癌细胞系的抗增殖活性。
(-)-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.