{"id":87975,"date":"2018-03-10T00:12:50","date_gmt":"2018-03-10T00:12:50","guid":{"rendered":"https:\/\/www.deberes.net\/tesis\/sin-categoria\/quirones-ciclohexanicos-a-partir-de-p-benzoquinona-sa%c2%adntesis-de-y-menisdaurilida-y-rengiolona\/"},"modified":"2018-03-10T00:12:50","modified_gmt":"2018-03-10T00:12:50","slug":"quirones-ciclohexanicos-a-partir-de-p-benzoquinona-sa%c2%adntesis-de-y-menisdaurilida-y-rengiolona","status":"publish","type":"post","link":"https:\/\/www.deberes.net\/tesis\/quimica\/quirones-ciclohexanicos-a-partir-de-p-benzoquinona-sa%c2%adntesis-de-y-menisdaurilida-y-rengiolona\/","title":{"rendered":"Quirones ciclohex\u00e1nicos a partir de p-benzoquinona. s\u00edntesis de (+) y (-)-menisdaurilida y (+)-rengiolona"},"content":{"rendered":"<h2>Tesis doctoral de <strong> Sonia Rodr\u00edguez Rodr\u00edguez <\/strong><\/h2>\n<p>La presente tesis doctoral forma parte de un proyecto de investigaci\u00f3n basado en el uso de p-benzoquinonas enmascaradas enantiopuras en el marco de la s\u00edntesis estereoselectiva de compuestos naturales. Para poder controlar la reactividad y la estereoselectividad en nuestro grupo se ha desarrollado una metodolog\u00eda eficiente consistente en la protecci\u00f3n de uno o ambos partes de grupos funcionales equivalentes de la p-benzoquinona.Dos de los monoacetales utilizados en este trabajo son (2r,3r)-2,3-difenil-1,4-dioxaesperio(4.5)deca-6,9-dien-8-ona, 20, derivado de un diol quiral con simetr\u00eda c2, y 10-feniltio-1,4-dioxaespiro(4.5)deca-6,9-dien-dien-8-ona, 22, respectivamente.  en esta tesis se ha demostrado que el grupo tiofenilo del monoacetal 22 act\u00faa eficazmente como p-benzoquinona enmascarada en reacciones de diels-alder. estas cicloadiciones pueden ser catalizadas por diversos \u00e1cidos de lewis y dan lugar exclusivamente a aductos endo con selectividades faciales que van de buenas a excelentes. Los productos pueden ser convertidos eficientemente en los cicloaductos formales de la p-benzoquinona, pero la racemizaci\u00f3n de 22 invalida esta metodolog\u00eda para la preparaci\u00f3nde aductos enantiopuros de diels-alder derivados de p-benzoquinona. Cuando el origen de la quiralidad se encuentra localizado en el anillo dioxol\u00e1nico, tal y como ocurre en 20, la inducci\u00f3n de asimetr\u00eda es moderada.  tambi\u00e9n se ha llevado a cabo un extenso estudio de la hidr\u00f3lisis de diversos acetales formados entre derivados de (+)-20 habi\u00e9ndose constatado la dificultad de llevar a cabo esta transformaci\u00f3n. El m\u00e9todo m\u00e1s eficaz es el uso de la arcilla montmorillonita k-10 en el seno de diclorometano.  finalmente, se han descrito los primeros ejemplos que demuestran la utilidad de los derivados ciclohex\u00e1nicos preparados: una nueva ruta de acceso a (r)-4-hidroxi-2-ciclohexen-1-ona y las primeras s\u00edntesis de los compuestos (+)- y (-)&#8211;menisdaurilida y (+)-rengi<\/p>\n<p>&nbsp;<\/p>\n<h3>Datos acad\u00e9micos de la tesis doctoral \u00ab<strong>Quirones ciclohex\u00e1nicos a partir de p-benzoquinona. s\u00edntesis de (+) y (-)-menisdaurilida y (+)-rengiolona<\/strong>\u00ab<\/h3>\n<ul>\n<li><strong>T\u00edtulo de la tesis:<\/strong>\u00a0 Quirones ciclohex\u00e1nicos a partir de p-benzoquinona. s\u00edntesis de (+) y (-)-menisdaurilida y (+)-rengiolona <\/li>\n<li><strong>Autor:<\/strong>\u00a0 Sonia Rodr\u00edguez Rodr\u00edguez <\/li>\n<li><strong>Universidad:<\/strong>\u00a0 Aut\u00f3noma de barcelona<\/li>\n<li><strong>Fecha de lectura de la tesis:<\/strong>\u00a0 15\/12\/2000<\/li>\n<\/ul>\n<p>&nbsp;<\/p>\n<h3>Direcci\u00f3n y tribunal<\/h3>\n<ul>\n<li><strong>Director de la tesis<\/strong>\n<ul>\n<li>Pere De March Centelles<\/li>\n<\/ul>\n<\/li>\n<li><strong>Tribunal<\/strong>\n<ul>\n<li>Presidente del tribunal: josep Font cierco <\/li>\n<li>tom\u00e1s Torres cebada (vocal)<\/li>\n<li>Francisco Palacios gambara (vocal)<\/li>\n<li>ramon Canela garayoa (vocal)<\/li>\n<\/ul>\n<\/li>\n<\/ul>\n<p>&nbsp;<\/p>\n","protected":false},"excerpt":{"rendered":"<p>Tesis doctoral de Sonia Rodr\u00edguez Rodr\u00edguez La presente tesis doctoral forma parte de un proyecto de investigaci\u00f3n basado en el [&hellip;]<\/p>\n","protected":false},"author":1,"featured_media":0,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"site-sidebar-layout":"default","site-content-layout":"","ast-site-content-layout":"","site-content-style":"default","site-sidebar-style":"default","ast-global-header-display":"","ast-banner-title-visibility":"","ast-main-header-display":"","ast-hfb-above-header-display":"","ast-hfb-below-header-display":"","ast-hfb-mobile-header-display":"","site-post-title":"","ast-breadcrumbs-content":"","ast-featured-img":"","footer-sml-layout":"","theme-transparent-header-meta":"","adv-header-id-meta":"","stick-header-meta":"","header-above-stick-meta":"","header-main-stick-meta":"","header-below-stick-meta":"","astra-migrate-meta-layouts":"default","ast-page-background-enabled":"default","ast-page-background-meta":{"desktop":{"background-color":"var(--ast-global-color-4)","background-image":"","background-repeat":"repeat","background-position":"center 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