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Molecules ; 29(8)2024 Apr 10.
Artículo en Inglés | MEDLINE | ID: mdl-38675534

RESUMEN

Bengamide E is a bioactive natural product that was isolated from Jaspidae sponges by Crews and co-workers in 1989. It displays a wide range of biological activities, including antitumor, antibiotic, and anthelmintic properties. With the aim of investigating the structural feature essential for their activity, several total syntheses of Bengamide E and its analogues have been reported in the literature. Nevertheless, no synthesis of the stereoisomer with modification of its configuration at C-4 carbon has been reported so far. Here, we report the first total synthesis of the 4-epi-Bengamide E. Key reactions in the synthesis include a chemoenzimatic desymmetrization of biobased starting materials and a diastereoselective Passerini reaction using a chiral, enantiomerically pure aldehyde, and a lysine-derived novel isocyanide.


Asunto(s)
Productos Biológicos , Estereoisomerismo , Estructura Molecular , Animales , Productos Biológicos/síntesis química , Productos Biológicos/química
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