Total synthesis of (-)-scabrolide A and (-)-yonarolide.

Hafeman, Nicholas J; Loskot, Steven A; Reimann, Christopher E; Pritchett, Beau P; Virgil, Scott C; Stoltz, Brian M

Hafeman, Nicholas J; Loskot, Steven A; Reimann, Christopher E; Pritchett, Beau P; Virgil, Scott C; Stoltz, Brian M.

Afiliación

Hafeman NJ; Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology Pasadena CA 91125 USA stoltz@caltech.edu.
Loskot SA; Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology Pasadena CA 91125 USA stoltz@caltech.edu.
Reimann CE; Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology Pasadena CA 91125 USA stoltz@caltech.edu.
Pritchett BP; Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology Pasadena CA 91125 USA stoltz@caltech.edu.
Virgil SC; Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology Pasadena CA 91125 USA stoltz@caltech.edu.
Stoltz BM; Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology Pasadena CA 91125 USA stoltz@caltech.edu.

Chem Sci ; 14(18): 4745-4758, 2023 May 10.

Article en En | MEDLINE | ID: mdl-37181769

RESUMEN

The complete account of the total syntheses of scabrolide A and yonarolide is disclosed. This article describes an initial approach involving a bio-inspired macrocyclization/transannular Diels-Alder cascade, which ultimately failed due to undesired reactivity during macrocycle construction. Next, the evolution of a second and third strategy, which both involve an initial intramolecular Diels-Alder reaction followed by a late-stage closure of the seven-membered ring of scabrolide A are detailed. The third strategy was first validated on a simplified system, but problems were encountered during a key [2 + 2] photocycloaddition on the fully elaborated system. An olefin protection strategy was employed to circumvent this problem, ultimately leading to the completion of the first total synthesis of scabrolide A and the closely related natural product yonarolide.

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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Chem Sci Año: 2023 Tipo del documento: Article Pais de publicación: Reino Unido

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