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Journal articles
Asymmetric Total Synthesis of Distaminolyne A and Revision of Its Absolute Configuration
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.
https://hal-polytechnique.archives-ouvertes.fr/hal-02090748
Contributor : Aurélien Arnoux Connect in order to contact the contributor
Submitted on : Friday, April 5, 2019 - 10:10:03 AM
Last modification on : Friday, January 7, 2022 - 3:47:22 AM
Contributor : Aurélien Arnoux Connect in order to contact the contributor
Submitted on : Friday, April 5, 2019 - 10:10:03 AM
Last modification on : Friday, January 7, 2022 - 3:47:22 AM