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

Dong-Yu Sun; Guan-Ying Han; Jing-Xu Gong; Bastien Nay; Xu-Wen Li; Yue-Wei Guo

doi:10.1021/acs.orglett.6b03892

Journal articles

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.

Document type :

Journal articles

Domain :

Chemical Sciences / Organic chemistry

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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

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

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

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