{"id":134839,"date":"1997-01-01T00:00:00","date_gmt":"1997-01-01T00:00:00","guid":{"rendered":"https:\/\/www.deberes.net\/tesis\/sin-categoria\/la-reaccion-de-polonovski-potier-sobre-n-oxidos-de-alcaloides-protoberberinicos-y-estudio-de-la-fotohidroximetilacion-de-isoquinolinios-sintesis-total-de-solidalina\/"},"modified":"1997-01-01T00:00:00","modified_gmt":"1997-01-01T00:00:00","slug":"la-reaccion-de-polonovski-potier-sobre-n-oxidos-de-alcaloides-protoberberinicos-y-estudio-de-la-fotohidroximetilacion-de-isoquinolinios-sintesis-total-de-solidalina","status":"publish","type":"post","link":"https:\/\/www.deberes.net\/tesis\/quimica\/la-reaccion-de-polonovski-potier-sobre-n-oxidos-de-alcaloides-protoberberinicos-y-estudio-de-la-fotohidroximetilacion-de-isoquinolinios-sintesis-total-de-solidalina\/","title":{"rendered":"La reaccion de polonovski-potier sobre n-oxidos de alcaloides protoberberinicos y estudio de la fotohidroximetilacion de isoquinolinios: sintesis total de solidalina."},"content":{"rendered":"<h2>Tesis doctoral de <strong> Francisco Najera Albendin <\/strong><\/h2>\n<p>Mediante la reaccion de polonovski-potier sobre los trans-n-oxidos de berbina se pueden obtener las correspondientes 7,8- deshidroberbinas, que se aislan como cianoderivados. Estas deshidroberbinas asi obtenidas permiten la sintesis de berbinas (8r*,14s*)-(+-)-8-metil y (8s*, 14s*)-(+-)-8- hidroximetil sustituidas con elevada diastereoselectividad.  se ha probado que en las condiciones de la reaccion de polonovski sobre trans-n- oxidos de berbina no se ve afectada la configuracion del c14, por lo que se ha podido llevar a cabo la sintesis de (8r,14s)-(-)-8-metilcanadina a partir de (-)-canadina.  la reaccion de polonovski sobre el cis-n-oxido de canadina produce 7,8- deshidrocanadina, 5-alfa- y 5-beta-hidroxicanadina. No se ha detectado en ningun caso la formacion de 6,7-deshidrocanadina.  la reduccion del producto de hidrolisis acida de (+-)-8-cianodihidroberberina, permite acceder a (8r*,14s*)-(+-)-8-hidroximetilcanadina con una estereoselectividad opuesta a la alcanzada a traves de la reaccion de polonovski.  la fotohidroximetilacion de sales de protoberberinio se produce exclusivamente sobre c8. La reduccion del iminio intermedio abre una ruta directa y diastereoselectiva a (8r*, 14s*)-(+-)-8-hidroximetilberbinas con buenos rendimientos.  se ha llevado a cabo la primera sintesis total de (+-)-solidalina mediante la fotohidroximetilacion del cloruro de deshidrocoridalina y la posterior oxidacion del producto de fotoadicion, lo que ha permitido establecer definitivamente la estructura de este alcaloide. Junto con (+-)-solidalina se ha obtenido su epimero en el c13 al que denominamos (+-)-episolidalina.<\/p>\n<p>&nbsp;<\/p>\n<h3>Datos acad\u00e9micos de la tesis doctoral \u00ab<strong>La reaccion de polonovski-potier sobre n-oxidos de alcaloides protoberberinicos y estudio de la fotohidroximetilacion de isoquinolinios: sintesis total de solidalina.<\/strong>\u00ab<\/h3>\n<ul>\n<li><strong>T\u00edtulo de la tesis:<\/strong>\u00a0 La reaccion de polonovski-potier sobre n-oxidos de alcaloides protoberberinicos y estudio de la fotohidroximetilacion de isoquinolinios: sintesis total de solidalina. <\/li>\n<li><strong>Autor:<\/strong>\u00a0 Francisco Najera Albendin <\/li>\n<li><strong>Universidad:<\/strong>\u00a0 M\u00e1laga<\/li>\n<li><strong>Fecha de lectura de la tesis:<\/strong>\u00a0 01\/01\/1997<\/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>Rafael Suau Suarez<\/li>\n<\/ul>\n<\/li>\n<li><strong>Tribunal<\/strong>\n<ul>\n<li>Presidente del tribunal: Juan Bosch Cartes <\/li>\n<li>Marcial Moreno Ma\u00f1as (vocal)<\/li>\n<li>Fernando Souto Bachiller (vocal)<\/li>\n<li>Mar\u00eda Valpuesta Fern\u00e1ndez (vocal)<\/li>\n<\/ul>\n<\/li>\n<\/ul>\n<p>&nbsp;<\/p>\n","protected":false},"excerpt":{"rendered":"<p>Tesis doctoral de Francisco Najera Albendin Mediante la reaccion de polonovski-potier sobre los trans-n-oxidos de berbina se pueden obtener las [&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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