Asymmetric Total Synthesis of Distaminolyne A and Revision of Its Absolute Configuration

详细信息    查看全文

• 作者：Dong-Yu Sun ; Guan-Ying Han ; Jing-Xu Gong ; Bastien Nay ; Xu-Wen Li ; Yue-Wei Guo
• 刊名：Organic Letters
• 出版年：2017
• 出版时间：February 3, 2017
• 年：2017
• 卷：19
• 期：3
• 页码：714-717
• 全文大小：322K
• ISSN：1523-7052

文摘

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 α-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.