{"id":26069,"date":"2003-01-10T00:00:00","date_gmt":"2003-01-10T00:00:00","guid":{"rendered":"https:\/\/www.deberes.net\/tesis\/sin-categoria\/sa%c2%adntesis-enantioselectiva-y-elucidacion-configuracional-de-los-terpenoides-nakamurol-a-y-xilarenal-a\/"},"modified":"2003-01-10T00:00:00","modified_gmt":"2003-01-10T00:00:00","slug":"sa%c2%adntesis-enantioselectiva-y-elucidacion-configuracional-de-los-terpenoides-nakamurol-a-y-xilarenal-a","status":"publish","type":"post","link":"https:\/\/www.deberes.net\/tesis\/barcelona\/sa%c2%adntesis-enantioselectiva-y-elucidacion-configuracional-de-los-terpenoides-nakamurol-a-y-xilarenal-a\/","title":{"rendered":"S\u00edntesis enantioselectiva y elucidaci\u00f3n configuracional de los terpenoides nakamurol a y xilarenal a"},"content":{"rendered":"<h2>Tesis doctoral de <strong> Sandra D\u00edaz Fite <\/strong><\/h2>\n<p>Durante la realizaci\u00f3n de la presente tesis doctoral se ha establecido que el m\u00e9todo m\u00e1s eficiente para la s\u00edntesis de la (4as, 5r)-4a,5-dimetil-4,4a, 5,6,7,8-hexahidronaftalen-2(3h)-ona (-)-3 desarrollado hasta el presente consiste en la doble alquilaci\u00f3n de la (r)-3-metilciclohexanona para generar un precursor de la lactona de enol bic\u00edclica de piers. La apertura de la misma por reacci\u00f3n con el derivado l\u00edtico del metilfosfonato de dimetilo y subsiguiente reacci\u00f3n de wadsworth-emmons intramolecular rinde al enona (-)-3 de manera satisfactoria.  por el contrario, para el acceso al enanti\u00f3mero (+)-3, el m\u00e9todo m\u00e1s eficiente consiste en la preparaci\u00f3n de la cetona de wieland-miescher y la transformaci\u00f3n del grupo carbonilo aislado en un grupo metilo mediante un proceso de integraci\u00f3n diastereoselectivo.  se ha establecido la configuraci\u00f3n relativa del c13 y la configuraci\u00f3n absoluta del diterpenoide (+)-nakamurol a , mediante s\u00edntesis total del (-)-nakamurol a. La identificaci\u00f3n de los datos de rmn (1h y 13c) comparando los descritos para el producto natural y el sintetizado as\u00ed como la medida del poder rotatorio del producto sintetizado permiten elucidar en base al proceso de s\u00edntesis la configuraci\u00f3n absoluta del producto natural. se ha determinado de forma inequ\u00edvoca la configuraci\u00f3n del c13 mediante un proceso de s\u00edntesis enantioespec\u00edfico que tiene como etapa clave una epoxidaci\u00f3n asim\u00e9trica de sharpless. La configuraci\u00f3n queda establecida no s\u00f3lo en base dela esperada selectividad en base al reactivo empleado, sino tambi\u00e9n por an\u00e1lisis pormenorizado de los datos de rmn. La primera s\u00edntesis total de nakamurol a, consta de 20 etapas. Tambi\u00e9n se ha establecido una ruta m\u00e1s corta (16 etapas) pero que carece de estereoselectividad en la formaci\u00f3n del centro estereog\u00e9nico en c13.  se ha establecido la configuraci\u00f3n absoluta del sesquiterpenoide xilarenal a mediante s\u00edntesis total y comprobaci\u00f3n d<\/p>\n<p>&nbsp;<\/p>\n<h3>Datos acad\u00e9micos de la tesis doctoral \u00ab<strong>S\u00edntesis enantioselectiva y elucidaci\u00f3n configuracional de los terpenoides nakamurol a y xilarenal a<\/strong>\u00ab<\/h3>\n<ul>\n<li><strong>T\u00edtulo de la tesis:<\/strong>\u00a0 S\u00edntesis enantioselectiva y elucidaci\u00f3n configuracional de los terpenoides nakamurol a y xilarenal a <\/li>\n<li><strong>Autor:<\/strong>\u00a0 Sandra D\u00edaz Fite <\/li>\n<li><strong>Universidad:<\/strong>\u00a0 Barcelona<\/li>\n<li><strong>Fecha de lectura de la tesis:<\/strong>\u00a0 01\/10\/2003<\/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>Asensio Gonz\u00e1lez Gazulla<\/li>\n<\/ul>\n<\/li>\n<li><strong>Tribunal<\/strong>\n<ul>\n<li>Presidente del tribunal: alejandro Fernandez barrero <\/li>\n<li>Francisco Foubelo Garc\u00eda (vocal)<\/li>\n<li>ester Lete exp\u00f3sito (vocal)<\/li>\n<li>f\u00e9lix Urp\u00ed tubella (vocal)<\/li>\n<\/ul>\n<\/li>\n<\/ul>\n<p>&nbsp;<\/p>\n","protected":false},"excerpt":{"rendered":"<p>Tesis doctoral de Sandra D\u00edaz Fite Durante la realizaci\u00f3n de la presente tesis doctoral se ha establecido que el m\u00e9todo [&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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