β-Selective C-Glycosylation and its Application in the Synthesis of ScleropentasideA
β-Selective C-Glycosylation and its Application in the Synthesis of ScleropentasideA
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DOI：
10.1002/anie.201900995
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发表时间：
2019-04-01
影响因子：
16.6
通讯作者：
Schuetzenmeister, Nina
中科院分区：
文献类型：
--
作者：
Boehlich, G. Jacob;Schuetzenmeister, Nina
c -糖苷是一种碳水化合物，它与在球端中心的糖基有一个C-C键。由于它们在化学和酶水解方面的高稳定性，这些化合物被广泛用作药物开发中的碳水化合物模拟物。在此，我们报道了一种合成天然丰富的酰基- c -糖苷结构基序的一般和专用β -选择性方法，该结构基序首次在硬壳蛋白天然产物家族中发现。Corey-Seebach umpolung反应是合成硬壳皂苷A及其类似物的关键步骤，使得β -选择性地从无保护的碳水化合物开始构建C-C键只需四个步骤。一锅法是高度原子效率，避免使用有毒重金属。
C-Glycosides are carbohydrates that bear a C-C bond to an aglycon at the anomeric center. Due to their high stability towards chemical and enzymatic hydrolysis, these compounds are widely used as carbohydrate mimics in drug development. Herein, we report a general and exclusively beta-selective method for the synthesis of a naturally abundant acyl-C-glycosidic structural motif first found in the scleropentaside natural product family. A Corey-Seebach umpolung reaction as the key step in the synthesis of scleropentaside A and analogues enables the beta-selective construction of the anomeric C-C bond starting from unprotected carbohydrates in only four steps. The one-pot approach is highly atom-efficient and avoids the use of toxic heavy metals.