{"id":39204,"date":"1999-01-01T00:00:00","date_gmt":"1999-01-01T00:00:00","guid":{"rendered":"https:\/\/www.deberes.net\/tesis\/sin-categoria\/sintesis-total-de-la-aglicona-del-sch-38516\/"},"modified":"1999-01-01T00:00:00","modified_gmt":"1999-01-01T00:00:00","slug":"sintesis-total-de-la-aglicona-del-sch-38516","status":"publish","type":"post","link":"https:\/\/www.deberes.net\/tesis\/quimica\/sintesis-total-de-la-aglicona-del-sch-38516\/","title":{"rendered":"Sintesis total de la aglicona del sch 38516."},"content":{"rendered":"<h2>Tesis doctoral de <strong>  Martin Carmona Manuel Alejo <\/strong><\/h2>\n<p>En la presente memoria se ha abordado con \u00e9xito la s\u00edntesis de la aglicona del sch 38516, una macrolactmaa de 13 carbonos con 4 centros estereog\u00e9nicos aislado a partir de la actinomadura vulgaris.  los centros estereog\u00e9nicos presentes en c2, c6 y c10 se han obtenido por reacciones de alquilaci\u00f3n estereoselectivas empleando como auxiliares quirales las oxazolidiononas desarrolladas por evans.  la siguiente etapa clave de la s\u00edntesis era la reacci\u00f3n ald\u00f3lica entre los fragmentos c1-c8 y c9-c13. El empleo de \u00e1cidos de lewis quirales, en concreto el desarrollado por gennari, derivado de la (-)-mentona, permiti\u00f3 aislar una mezcla de aldoles con uan conversi\u00f3n del 79% y un e.D. del 91%.  una serie de itnerconversiones de grupos funcionales llev\u00f3 al azido\u00e1cido precursor de la siguiente etapa clave de la s\u00edntesis: la reacci\u00f3n de macrolactamizaci\u00f3n, donde se emplearon diferentes metodolog\u00edas desarrolladas en nuestro grupo de investigaci\u00f3n. En concreto, cuando se activ\u00f3 el grupo carboxilo como tio\u00e9ster de s-2-piridilo y el grupo azida se redujo con un complejo de esta\u00f1o (ii) se consigui\u00f3 un 73% de lactama.  las \u00faltimas etapas de la s\u00edntesis fueron una serie de interconversiones de grupos funcionales que permiti\u00f3 llegar a la aglicona del sch 38516 con un rendimiento global del 6% en 24 etapas.  la preparaci\u00f3n de un derivado acetilado en el hidroxilo en c9 permiti\u00f3 correlacionar los datos espectrosc\u00f3picos de la mol\u00e9cula sintetizada con los descritos en la literatura.<\/p>\n<p>&nbsp;<\/p>\n<h3>Datos acad\u00e9micos de la tesis doctoral \u00ab<strong>Sintesis total de la aglicona del sch 38516.<\/strong>\u00ab<\/h3>\n<ul>\n<li><strong>T\u00edtulo de la tesis:<\/strong>\u00a0 Sintesis total de la aglicona del sch 38516. <\/li>\n<li><strong>Autor:<\/strong>\u00a0  Martin Carmona Manuel Alejo <\/li>\n<li><strong>Universidad:<\/strong>\u00a0 Barcelona<\/li>\n<li><strong>Fecha de lectura de la tesis:<\/strong>\u00a0 01\/01\/1999<\/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>Jaume Vilarrasa Llorens<\/li>\n<\/ul>\n<\/li>\n<li><strong>Tribunal<\/strong>\n<ul>\n<li>Presidente del tribunal: mario Rubiralta alca\u00f1iz <\/li>\n<li>marti Bartra sanmati (vocal)<\/li>\n<li>julio Delgado mart\u00edn (vocal)<\/li>\n<li>pere de March centelles (vocal)<\/li>\n<\/ul>\n<\/li>\n<\/ul>\n<p>&nbsp;<\/p>\n","protected":false},"excerpt":{"rendered":"<p>Tesis doctoral de Martin Carmona Manuel Alejo En la presente memoria se ha abordado con \u00e9xito la s\u00edntesis de la [&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 center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-gradient":""},"tablet":{"background-color":"","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-gradient":""},"mobile":{"background-color":"","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-gradient":""}},"ast-content-background-meta":{"desktop":{"background-color":"var(--ast-global-color-5)","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-gradient":""},"tablet":{"background-color":"var(--ast-global-color-5)","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-gradient":""},"mobile":{"background-color":"var(--ast-global-color-5)","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-gradient":""}},"footnotes":""},"categories":[951,332,305,17,416,9297],"tags":[1383,8263,13655,101200,101199,13656],"class_list":["post-39204","post","type-post","status-publish","format-standard","hentry","category-barcelona","category-ciencias-tecnologicas","category-ingenieria-y-tecnologia-quimicas","category-quimica","category-quimica-organica","category-sintesis-quimica","tag-jaume-vilarrasa-llorens","tag-julio-delgado-martin","tag-mario-rubiralta-alcaniz","tag-marti-bartra-sanmati","tag-martin-carmona-manuel-alejo","tag-pere-de-march-centelles"],"_links":{"self":[{"href":"https:\/\/www.deberes.net\/tesis\/wp-json\/wp\/v2\/posts\/39204","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/www.deberes.net\/tesis\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.deberes.net\/tesis\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.deberes.net\/tesis\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/www.deberes.net\/tesis\/wp-json\/wp\/v2\/comments?post=39204"}],"version-history":[{"count":0,"href":"https:\/\/www.deberes.net\/tesis\/wp-json\/wp\/v2\/posts\/39204\/revisions"}],"wp:attachment":[{"href":"https:\/\/www.deberes.net\/tesis\/wp-json\/wp\/v2\/media?parent=39204"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.deberes.net\/tesis\/wp-json\/wp\/v2\/categories?post=39204"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.deberes.net\/tesis\/wp-json\/wp\/v2\/tags?post=39204"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}