Asymmetric Total Synthesis of Distaminolyne A and Revision of Its Absolute Configuration
Asymmetric Total Synthesis of Distaminolyne A and Revision of Its Absolute Configuration
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Distaminolyne A 的不对称全合成及其绝对构型的修正
DOI：
10.1021/acs.orglett.6b03892
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发表时间：
2017-02-03
期刊：
影响因子：
5.2
通讯作者：
Guo, Yue-Wei
中科院分区：
文献类型：
--
作者：
Sun, Dong-Yu;Han, Guan-Ying;Guo, Yue-Wei
从市售的10 - 十一碳烯 - 1 - 醇出发，实现了一种海洋来源的多炔化合物——二胺炔A及其对映体的首次全合成。在合成对映体纯的1,2 - 氨基醇的过程中，利用了脯氨酸催化的醛中间体的不对称α - 氨基氧化反应来引入手性中心。通过使用手性衍生化试剂确定了二胺炔A的两种合成对映体的绝对构型，从而将天然产物的绝对构型从2S修订为2R。对其抗菌、胰脂肪酶（PL）抑制和蛋白酪氨酸磷酸酶1B（PTP1B）抑制活性进行了评估。
The first total synthesis of a marine derived polyacetylene, distaminolyne A, and its enantiomer were achieved from the commercially available undec-10-en-1-ol. A key proline-catalyzed asymmetric alpha-aminooxylation of an aldehyde intermediate was used to introduce the chiral center en route to the enantiomerically pure 1,2-amino alcohols. The absolute configuration of both synthesized enantiomers of distaminolyne A was confirmed by using chiral derivatizing agents, leading to revision of the natural product absolute configuration from 2S to 2R. Antibacterial, pancreatic lipase (PL) inhibitory, and protein-tyrosine phosphatase 1B (PTP1B) inhibitory activities were evaluated.