Synthetic Studies on Novel, Natural Anti-Mitotic Agents, Nigricanosides, toward Elucidation of Their Stereochemistry and Biological Activity

从绿色黑藻Avrainvillea nigricans中分离得到的黑藻糖类化合物属于单半乳糖二酰甘油家族，对肿瘤细胞具有很强的生长抑制活性。由于天然来源的稀缺性和未知的立体化学，黑素苷类化合物还没有得到详细的生物学研究。因此，旨在阐明它们的立体化学和生物活性的研究已经从部分合成同系物黑素A二甲酯开始。因此，建立了两个醚键的构建方法，并阐明了半乳糖部分与低位酰基链之间的乙醚连接的立体化学。

Nigricanoseides, isolated from the green alga Avrainvillea nigricans, belong to a monogalactosyldiacylglycerol family and exhibit potent growth inhibitory activity against cancer cells. Because of the scarce supply from natural source and the unknown stereochemistry, nigricanosides are not explored biologically in detail. Therefore, studies aiming at the elucidation of their stereochemistry and biological activity have commenced with the partial synthesis of a congener, nigricanoseide A dimethyl ester. As a result, methods for the construction of the two ether linkages have been established, and the stereochemistry of the ether junction between the galactose moiety and the lower acyl chain has been clarified.