{"id":96774,"date":"2018-03-11T10:17:08","date_gmt":"2018-03-11T10:17:08","guid":{"rendered":"https:\/\/www.deberes.net\/tesis\/sin-categoria\/sa%c2%adntesis-de-la-espirolabdanolida-leopersin-d-y-otros-labdanos-di-tri-y-tetraoxigenados-en-el-anillo-b\/"},"modified":"2018-03-11T10:17:08","modified_gmt":"2018-03-11T10:17:08","slug":"sa%c2%adntesis-de-la-espirolabdanolida-leopersin-d-y-otros-labdanos-di-tri-y-tetraoxigenados-en-el-anillo-b","status":"publish","type":"post","link":"https:\/\/www.deberes.net\/tesis\/mecanismos-de-las-reacciones-organicas\/sa%c2%adntesis-de-la-espirolabdanolida-leopersin-d-y-otros-labdanos-di-tri-y-tetraoxigenados-en-el-anillo-b\/","title":{"rendered":"S\u00edntesis de la espirolabdanolida leopersin d y otros labdanos di, tri y tetraoxigenados en el anillo b"},"content":{"rendered":"<h2>Tesis doctoral de <strong> Lourdes Casta\u00f1eda Garcia <\/strong><\/h2>\n<p>En el presente trabajo se describe la s\u00edntesis, a partir de esclareol, de labdanos di, tri y tetraoxigenados en el anillo b con funciones en c-6 y c-7. Se han sintetizado siete labdanos naturales altamente oxigenados en el anillo b que presentan en la cadena lateral agrupaciones al\u00edlicas, g-hidroxibutenolidas, furanos o espirobutanolidas, adem\u00e1s de algunos dinorlabdanos tetraoxigenados en el anillo b, que son intermedios avanzados hacia la s\u00edntesis de forskolin. estas s\u00edntesis han permitido establecer la estructura de 6-acetoxi-labda-8,14-dieno- 7,13r-diol para el producto natural aislado de haplopappus parvifolious corrigiendo la originalmente propuesta. Adem\u00e1s se ha corroborado la estructura y se ha establecido la configuraci\u00f3n absoluta de los productos naturales (+)-triacetato de labda-8,13z-dien-6,7,15- ilo, (+)-sibiricinona a, (+)-sibiricinona b, (+)-leoheterin y (+)-leopersin d. las s\u00edntesis de estos labdanos altamente oxigenados en el anillo b se han realizado empleando una nueva estrategia que permite obtener 6,7-dioles a-cis y b-cis, as\u00ed como transformar los primeros en los segundos con excelente rendimiento. Por inversi\u00f3n en c-7 de los dioles b-cis se han obtenido compuestos con las funciones oxigenadas de c-6 y c-7 en disposici\u00f3n trans-diaxial. respecto a las cadenas laterales de los productos naturales, el control en la estereoqu\u00edmica de la agrupaci\u00f3n al\u00edlica se ha realizado a trav\u00e9s de la epoxidaci\u00f3n asim\u00e9trica de sharpless o utilizando como auxiliar quiral taddol, las g-hidroxibutenolidas han sido elaboradas a trav\u00e9s de la metodolog\u00eda de bestmann seguida de la de faulkner y las dioxoespirobutanolidas por reacci\u00f3n de oxo-michael intramolecular. adem\u00e1s, se han realizado pruebas de actividad de 17 compuestos sintetizados en este trabajo, encontrando que los compuestos que presentan un anillo b similar al de forskolin muestran una actividad antitumoral moderada.<\/p>\n<p>&nbsp;<\/p>\n<h3>Datos acad\u00e9micos de la tesis doctoral \u00ab<strong>S\u00edntesis de la espirolabdanolida leopersin d y otros labdanos di, tri y tetraoxigenados en el anillo b<\/strong>\u00ab<\/h3>\n<ul>\n<li><strong>T\u00edtulo de la tesis:<\/strong>\u00a0 S\u00edntesis de la espirolabdanolida leopersin d y otros labdanos di, tri y tetraoxigenados en el anillo b <\/li>\n<li><strong>Autor:<\/strong>\u00a0 Lourdes Casta\u00f1eda Garcia <\/li>\n<li><strong>Universidad:<\/strong>\u00a0 Salamanca<\/li>\n<li><strong>Fecha de lectura de la tesis:<\/strong>\u00a0 23\/10\/2009<\/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>Isidro Sanchez Marcos<\/li>\n<\/ul>\n<\/li>\n<li><strong>Tribunal<\/strong>\n<ul>\n<li>Presidente del tribunal: arturo San feliciano martin <\/li>\n<li>Antonio Abad somovilla (vocal)<\/li>\n<li>Andr\u00e9s Parra sanchez (vocal)<\/li>\n<li>Mar\u00eda del carmen Avenda\u00f1o l\u00f3pez (vocal)<\/li>\n<\/ul>\n<\/li>\n<\/ul>\n<p>&nbsp;<\/p>\n","protected":false},"excerpt":{"rendered":"<p>Tesis doctoral de Lourdes Casta\u00f1eda Garcia En el presente trabajo se describe la s\u00edntesis, a partir de esclareol, de labdanos [&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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