De Novo Asymmetric Synthesis and Biological Evaluation of the Trisaccharide Portion of PI-080 and Vineomycin B2
De Novo Asymmetric Synthesis and Biological Evaluation of the Trisaccharide Portion of PI-080 and Vineomycin B2
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DOI：
10.1021/ol801817f
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发表时间：
2008-10-16
期刊：
影响因子：
5.2
通讯作者：
O'Doherty, George A.
中科院分区：
文献类型：
--
作者：
Yu, Xiaomei;O'Doherty, George A.
本文报道了一种具有高度对映体和非对映选择性的α-L-针叶糖、α-L红景天糖和β-D-橄榄糖三糖的合成方法。关键的转化包括钯催化的糖基化、Myers还原重排、非对映选择性二羟基化和区域选择性Mitsunobu反转。该三糖具有明显的抗肿瘤细胞凋亡活性，这可能与长春霉素B2和PI-080的构效关系有关。
A highly enantio- and diastereoselective synthesis of an alpha-L-aculose, alpha-L-rhodinose, and beta-D-olivose trisaccharide is described. The key transformations include the palladium-catalyzed glycosylation, Myers' reductive rearrangement, diastereoselective dihydroxylation, and regioselective Mitsunobu inversion. Significant apoptotic antitumor activity was found for this trisaccharide, which has implication for vineomycin B2 and PI-080 structure-activity relationship.