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A Convergent Total Synthesis of (+)-Ineleganolide

[Image: see text] We report the total synthesis of the furanobutenolide-derived diterpenoid (+)-ineleganolide. The synthetic approach relies on a convergent strategy based on the coupling of two enantioenriched fragments, which are derived from (−)-linalool and (+)-norcarvone, respectively. A high-y...

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Detalles Bibliográficos
Autores principales: Gross, Benjamin M., Han, Seo-Jung, Virgil, Scott C., Stoltz, Brian M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10544024/
https://www.ncbi.nlm.nih.gov/pubmed/36989438
http://dx.doi.org/10.1021/jacs.3c02142
Descripción
Sumario:[Image: see text] We report the total synthesis of the furanobutenolide-derived diterpenoid (+)-ineleganolide. The synthetic approach relies on a convergent strategy based on the coupling of two enantioenriched fragments, which are derived from (−)-linalool and (+)-norcarvone, respectively. A high-yielding, one-step Michael addition and aldol cascade furnishes a pentacyclic framework as a single diastereomer, thereby overcoming previous challenges in controlling stereochemistry. The endgame features an O(2)-facilitated C–H oxidation and a samarium diiodide-induced semipinacol rearrangement to furnish the highly rigid central seven-membered ring.