AI Article Synopsis
- Bengamide E is a bioactive compound from Jaspidae sponges, known for its antitumor, antibiotic, and anthelmintic properties, first isolated by Crews et al. in 1989.
- Various total syntheses of Bengamide E and its analogues have been explored, but none have successfully synthesized a stereoisomer with a modified configuration at the C-4 carbon until now.
- This study presents the first total synthesis of the 4--Bengamide E, employing key reactions like chemoenzymatic desymmetrization and a diastereoselective Passerini reaction with a chiral aldehyde and a new lysine-derived isocyanide.
Article Abstract
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--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.
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Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC11052282 | PMC |
| http://dx.doi.org/10.3390/molecules29081715 | DOI Listing |
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