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

Dong-Yu Sun 1, 2 Guan-Ying Han 3 Jing-Xu Gong 1 Bastien Nay 4 Xu-Wen Li 1, * Yue-Wei Guo 1, *
* Corresponding author
1 State Key Laboratory of Drug Research
2 School of Pharmaceutical Sciences
3 First Affiliated Hospital of Jinzhou Medical University
4 DCSO - Laboratoire de synthèse organique
Abstract : 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.
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https://hal-polytechnique.archives-ouvertes.fr/hal-02090748
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Submitted on : Friday, April 5, 2019 - 10:10:03 AM
Last modification on : Friday, April 12, 2019 - 1:31:46 AM

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Dong-Yu Sun, Guan-Ying Han, Jing-Xu Gong, Bastien Nay, Xu-Wen Li, et al.. Asymmetric Total Synthesis of Distaminolyne A and Revision of Its Absolute Configuration. Organic Letters, American Chemical Society, 2017, 19 (3), pp.714-717. ⟨10.1021/acs.orglett.6b03892⟩. ⟨hal-02090748⟩

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