{"id":2151,"date":"1994-01-01T00:00:00","date_gmt":"1994-01-01T00:00:00","guid":{"rendered":"https:\/\/www.deberes.net\/tesis\/1994\/01\/01\/sintesis-diastereo-y-enantioselectiva-de-los-cuatro-diastereoisomeros-del-alfa-aminoester-n-terminal-de-las-nikomicinas-b-y-bx-y-sistemas-relacionados\/"},"modified":"1994-01-01T00:00:00","modified_gmt":"1994-01-01T00:00:00","slug":"sintesis-diastereo-y-enantioselectiva-de-los-cuatro-diastereoisomeros-del-alfa-aminoester-n-terminal-de-las-nikomicinas-b-y-bx-y-sistemas-relacionados","status":"publish","type":"post","link":"https:\/\/www.deberes.net\/tesis\/quimica\/sintesis-diastereo-y-enantioselectiva-de-los-cuatro-diastereoisomeros-del-alfa-aminoester-n-terminal-de-las-nikomicinas-b-y-bx-y-sistemas-relacionados\/","title":{"rendered":"Sintesis diastereo y enantioselectiva de los cuatro diastereoisomeros del alfa-aminoester n-terminal de las nikomicinas b y bx y sistemas relacionados"},"content":{"rendered":"<h2>Tesis doctoral de <strong> Argimiro Lopez Viado <\/strong><\/h2>\n<p>En esta memoria se recoge la aplicacion de la metodolog\u00eda desarrollada para obtener gamma-aminoalcoholes con tres estereocentros, a partir de 1-aza-1,3-butadienos y aldehidos quirales, en la sintesis diastereo- y enantioselectiva del alfa-amino-gamma-hidroxiester n-terminal de dos antibioticos naturales, las nikomicinas b y bx. Del mismo modo, se preparan tambien sus tres posibles diastereoisomeros.  en el primer capitulo se aborda la preparacion de las beta-aminocetonas syn y anti, precursoras de los productos finales, con dos centros quirales, a partir del 1-aza-1,3-butadieno adecuado, via la correspondiente dihidropirimidina y tetrahidropirimidina. En primer lugar, se pone a punto un metodo para preparar, con buenos rendimientos, el azabutadieno idoneo para nuestros fines, el cual presenta un resto furilo como precursor de la funcion carboxilica. A continuacion, se sintetiza la correspondiente dihidropirimidina quiral por reaccion entre el azabutadieno y el aldehido (r)-(+)-o-bencil lactico. Posteriormente, la reduccion de esta da lugar a la tetrahidropirimidina, (creandose asi el primer estereocentro), que se hidroliza, obteniendose las b-aminocetonas syn y anti, con la consiguiente generacion del segundo centro asimetrico.  en el segundo capitulo se aborda la creacion del tercer centro quiral. Esto se lleva a cabo a traves de la reduccion diastereoselectiva de las dos b-aminocetonas anteriormente preparadas. Asi, se obtienen cuatro gamma-aminoalcoholes, dos provenientes de la b-aminocetona syn y dos de la beta-aminocetona anti. A partir de estos se sintetizan las correspondientes aminolactonas por oxidacion del resto furilo. Finalmente, se preparan los alfa-amino-gamma-hidroxiesteres metilicos cuando la oxidacion del resto furilo se efectua sobre los gamma-aminoalcoholes con el grupo hidroxilo protegido.  por ultimo se anticipa la iniciacion de un plan sintetico paralelo, partiendo de un 4-amino-1-azabutadieno que tiene<\/p>\n<p>&nbsp;<\/p>\n<h3>Datos acad\u00e9micos de la tesis doctoral \u00ab<strong>Sintesis diastereo y enantioselectiva de los cuatro diastereoisomeros del alfa-aminoester n-terminal de las nikomicinas b y bx y sistemas relacionados<\/strong>\u00ab<\/h3>\n<ul>\n<li><strong>T\u00edtulo de la tesis:<\/strong>\u00a0 Sintesis diastereo y enantioselectiva de los cuatro diastereoisomeros del alfa-aminoester n-terminal de las nikomicinas b y bx y sistemas relacionados <\/li>\n<li><strong>Autor:<\/strong>\u00a0 Argimiro Lopez Viado <\/li>\n<li><strong>Universidad:<\/strong>\u00a0 Oviedo<\/li>\n<li><strong>Fecha de lectura de la tesis:<\/strong>\u00a0 01\/01\/1994<\/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>Jos\u00e9 Joaquin Barluenga Mur<\/li>\n<\/ul>\n<\/li>\n<li><strong>Tribunal<\/strong>\n<ul>\n<li>Presidente del tribunal: Julio Delgado Mart\u00edn <\/li>\n<li>Antonio Mouri\u00f1o Mosquera (vocal)<\/li>\n<li>Pedro Molina Buend\u00eda (vocal)<\/li>\n<li>Francisco Campos Diaz (vocal)<\/li>\n<\/ul>\n<\/li>\n<\/ul>\n<p>&nbsp;<\/p>\n","protected":false},"excerpt":{"rendered":"<p>Tesis doctoral de Argimiro Lopez Viado En esta memoria se recoge la aplicacion de la metodolog\u00eda desarrollada para obtener gamma-aminoalcoholes [&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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