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Síntesis total, asignación de la estereoquímica relativa y absoluta y reasignación estructural de la fostriecina

Christopher P Burke¹, Nadia Haq, Dale L Boger

¹Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.

Journal of the American Chemical Society

|January 30, 2010

Resumen

Los investigadores informan de la síntesis total de la phostriecin (fosfato monoéster) y la sultriecin (sulfato monoéster), aclarando el phostriecin.

Área de la Ciencia:

Química orgánica es la química orgánica.
Síntesis de Productos Naturales.
Química Medicinal La Química Medicinal es un campo de estudio de la química medicinal.

Sus antecedentes:

La fostriecina, anteriormente identificada como sultriecina, es un producto natural con actividad biológica potencial.
La asignación estructural inicial como un monoester de sulfato requirió una reevaluación.

Objetivo del estudio:

Para lograr la síntesis total de la fostriecina y la sultriecina.
Para reasignar la estructura de la phostriecin como un monoestero de fosfato.
Para establecer la estereoquímica relativa y absoluta de la fostriecina.

Principales métodos:

Síntesis total asimétrica convergente y convergente.
Alilación marrón para la estereoquímica C9.
Reducción asimétrica de la CBS para la estereoquímica de la lactona C5.
Expansión del anillo oxidativo de un alfa-hidroxifuran.
Adición de cuprato controlada por quelación para instalación de trieno.

Principales resultados:

Síntesis exitosa tanto del monoestero sulfato (1) asignado originalmente como del monoestero fosfato (2) reasignado.
Utilizó la espectroscopia de RMN de 1H para asignaciones estructurales y estereoquímicas.
Estableció la unidad de Z,Z,E-trieno y los estereocentros en C5, C9 y C11.

Conclusiones:

El estudio proporciona una síntesis inequívoca de la phostriecin y la sultriecin, confirmando la estructura del monoester de fosfato de la phostriecin.
La vía sintética permite la preparación de análogos para estudiar la inhibición de la proteína fosfatasa 2A.

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