Total Synthesis and Structural Revision of (±)-Mauritamide B.
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| Format: | Artículo científico |
| Sprache: | en |
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Journal of natural products
2025
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| _version_ | 1868266239838650368 |
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| author | Hirozumi, Ryosuke Kudo, Yuta Cho, Yuko Konoki, Keiichi Yotsu-Yamashita, Mari |
| author_facet | Hirozumi, Ryosuke Kudo, Yuta Cho, Yuko Konoki, Keiichi Yotsu-Yamashita, Mari Hirozumi, Ryosuke Kudo, Yuta Cho, Yuko Konoki, Keiichi Yotsu-Yamashita, Mari |
| collection | PubMed - marine biology |
| contents | Total Synthesis and Structural Revision of (±)-Mauritamide B. Hirozumi, Ryosuke Kudo, Yuta Cho, Yuko Konoki, Keiichi Yotsu-Yamashita, Mari Molecular Structure Animals Pyrroles Alkaloids Agelas Stereoisomerism Marine Biology Mauritamide B () is a taurine-connected cyclic guanidino-bromopyrrole alkaloid originally isolated from the marine sponge . To date, the total synthesis of taurine-connected guanidino-bromopyrrole alkaloids, including this compound, has not yet been reported. Herein, a total synthesis of (±)-mauritamide B () was achieved by oxidation of 2-aminoimidazole of dihydro-sventrin () using activated carbon and air in the presence of taurine. The synthetic precursor of , 4-(3-aminopropyl)-2-aminoimidazole (), was synthesized via our original route. The NMR data of the obtained product agreed with that reported for mauritamide B (). However, a detailed analysis of the NMR data of synthetic (±)-mauritamide B () including H-N HSQC spectrum revealed the need for a structural revision of the reported structure for mauritamide B (). |
| format | Artículo científico |
| id | pubmed_39981783 |
| institution | PubMed |
| language | en |
| publishDate | 2025 |
| publisher | Journal of natural products |
| record_format | pubmed |
| spellingShingle | Total Synthesis and Structural Revision of (±)-Mauritamide B. Hirozumi, Ryosuke Kudo, Yuta Cho, Yuko Konoki, Keiichi Yotsu-Yamashita, Mari Molecular Structure Animals Pyrroles Alkaloids Agelas Stereoisomerism Marine Biology Total Synthesis and Structural Revision of (±)-Mauritamide B. Hirozumi, Ryosuke Kudo, Yuta Cho, Yuko Konoki, Keiichi Yotsu-Yamashita, Mari Molecular Structure Animals Pyrroles Alkaloids Agelas Stereoisomerism Marine Biology Mauritamide B () is a taurine-connected cyclic guanidino-bromopyrrole alkaloid originally isolated from the marine sponge . To date, the total synthesis of taurine-connected guanidino-bromopyrrole alkaloids, including this compound, has not yet been reported. Herein, a total synthesis of (±)-mauritamide B () was achieved by oxidation of 2-aminoimidazole of dihydro-sventrin () using activated carbon and air in the presence of taurine. The synthetic precursor of , 4-(3-aminopropyl)-2-aminoimidazole (), was synthesized via our original route. The NMR data of the obtained product agreed with that reported for mauritamide B (). However, a detailed analysis of the NMR data of synthetic (±)-mauritamide B () including H-N HSQC spectrum revealed the need for a structural revision of the reported structure for mauritamide B (). |
| title | Total Synthesis and Structural Revision of (±)-Mauritamide B. |
| topic | Molecular Structure Animals Pyrroles Alkaloids Agelas Stereoisomerism Marine Biology |
| url | https://pubmed.ncbi.nlm.nih.gov/39981783/ |