Ring-closing metathesis studies in the context of the formal synthesis of themarine macrolide (–)-callyspongiolide
Attempts to synthesize the natural product macrolide polyketide (–)-callyspongiolide have drawn great interest</p><p>because of its potent cytotoxic activity. Its total synthesis has proven to be difficult, however, due to its</p><p>challenging structure. The influence of the...
| Autores: | , , , , |
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| Tipo de recurso: | artículo |
| Estado: | Versión publicada |
| Fecha de publicación: | 2025 |
| País: | España |
| Institución: | Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya) |
| Repositorio: | Recercat. Dipósit de la Recerca de Catalunya |
| OAI Identifier: | oai:recercat.cat:2445/227643 |
| Acceso en línea: | https://hdl.handle.net/2445/227643 |
| Access Level: | acceso abierto |
| Palabra clave: | Metàtesi (Química) Compostos bioactius Síntesi orgànica Alcaloides Metathesis (Chemistry) Bioactive compounds Organic synthesis Alkaloids |
| Sumario: | Attempts to synthesize the natural product macrolide polyketide (–)-callyspongiolide have drawn great interest</p><p>because of its potent cytotoxic activity. Its total synthesis has proven to be difficult, however, due to its</p><p>challenging structure. The influence of the configuration of a homoallylic stereocenter on the closure of a 14-</p><p>membered macrocyclic carbonate by ring-closing metathesis (RCM) from two epimeric dienes is described. The</p><p>results offer some insights into the structural features which contribute to hampering the closure of the</p><p>macrocyclic core of the macrolide polyketide. A formal synthesis of the marine macrolide (–)-callyspongiolide is</p><p>also reported using a RCM approach (C10-C11 bond formed) from analogous dienes bearing an α,β-unsaturated</p><p>ester instead of a carbonate |
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