{"id":30525,"date":"2004-04-06T00:00:00","date_gmt":"2004-04-06T00:00:00","guid":{"rendered":"https:\/\/www.deberes.net\/tesis\/sin-categoria\/sa%c2%adntesis-de-quinonas-tetra-y-pentaca%c2%adclicas-con-quiralidad-helicoidal-a-partir-de-ss-2-p-tolilsulfinil-14-benzoquinonas\/"},"modified":"2004-04-06T00:00:00","modified_gmt":"2004-04-06T00:00:00","slug":"sa%c2%adntesis-de-quinonas-tetra-y-pentaca%c2%adclicas-con-quiralidad-helicoidal-a-partir-de-ss-2-p-tolilsulfinil-14-benzoquinonas","status":"publish","type":"post","link":"https:\/\/www.deberes.net\/tesis\/sin-categoria\/sa%c2%adntesis-de-quinonas-tetra-y-pentaca%c2%adclicas-con-quiralidad-helicoidal-a-partir-de-ss-2-p-tolilsulfinil-14-benzoquinonas\/","title":{"rendered":"S\u00edntesis de quinonas tetra y pentac\u00edclicas con quiralidad helicoidal a partir de (ss)-2-(p-tolilsulfinil)-1,4-benzoquinonas"},"content":{"rendered":"<h2>Tesis doctoral de <strong>  Garc\u00eda Cerrada Susana M. <\/strong><\/h2>\n<p>1,- se han establecido dos accesos complementarios a las dihidro[5]helicenoquinonas y bisquinonas enantiom\u00e9ricamente puras, basados en el proceso domin\u00f3 de reacci\u00f3n de diels-alder\/eliminaci\u00f3n pirol\u00edtica del sulf\u00f3xido\/aromatizaci\u00f3n que tiene lugar cuando un dieno adecuadamente sustituido reacciona con la (ss)-2-(p-tolilsulfinil)-1,4-benzoquinona enantiom\u00e9ricamente pura.  1.1,- en el primero de ellos, el dieno implicado es el 1,4-divinil-1,3-ciclohexadieno. su reacci\u00f3n con el filodieno quiral permite acceder en una \u00fanica etapa al sistema de (m)-dihidro[5]helicenobisquinona con un rendimiento global del 3.8% y una pureza \u00f3ptica del 50%.  1.2,- la otra ruta de s\u00edntesis se lleva a cabo de forma secuencial a partir de la (ss)-2-(p-tolilsulfinil)-1,4-benzoquinona, utilizando como dieno un sistema de vinildihidrofenantreno 1,4-dialcoxisustituido o de vinildihidrofenantrnoquinona.  1.2.1,- a partir del derivado de vinildihidrofenantrenoquinona, se obtiene la (m)-dihidro[5]helicenobisquinona con un rendimiento global del 4.6% y un 74% de exceso enantiom\u00e9rico.  1.2.2,- a partir del vinildihidrofenantreno 1,4-dimetoxi sustituido, se ha sintetizado la (p)-dihidro[5]helicenoquinona 101 con un rendimiento global del 34% y un 84% de exceso enantiom\u00e9rico y el derivado etoxi sustituido (p)-106 con un rendimiento global del 23% y 92% de exceso enantiom\u00e9rico.  1.2.3,- a partir del vnildihidrofenantreno 1,4-bis-terc-butil dimetil sililoxi sustituido se ha sintetizado la (p)-dihidro[5]helicenoquinona 108 con un rendimiento global del 21% y un 98% de exceso enantiom\u00e9rico.  1.2.4,- esta s\u00edntesis por etapas permite aislar los intermedios pentac\u00edclicos resulantes del proceso domini\u00f3 reacci\u00f3n de diels-alder\/eliminaci\u00f3n pirol\u00edtica del sulf\u00f3xido. A partir de estos compuestos tetrahidroarom\u00e1ticos, es posible la s\u00edntesis enantiodivergente de los dos hel\u00edmeros (p) o (m) de la [5]helicenoquinona o bisquinona final, simplemente seleccionando<\/p>\n<p>&nbsp;<\/p>\n<h3>Datos acad\u00e9micos de la tesis doctoral \u00ab<strong>S\u00edntesis de quinonas tetra y pentac\u00edclicas con quiralidad helicoidal a partir de (ss)-2-(p-tolilsulfinil)-1,4-benzoquinonas<\/strong>\u00ab<\/h3>\n<ul>\n<li><strong>T\u00edtulo de la tesis:<\/strong>\u00a0 S\u00edntesis de quinonas tetra y pentac\u00edclicas con quiralidad helicoidal a partir de (ss)-2-(p-tolilsulfinil)-1,4-benzoquinonas <\/li>\n<li><strong>Autor:<\/strong>\u00a0  Garc\u00eda Cerrada Susana M. <\/li>\n<li><strong>Universidad:<\/strong>\u00a0 Aut\u00f3noma de Madrid<\/li>\n<li><strong>Fecha de lectura de la tesis:<\/strong>\u00a0 04\/06\/2004<\/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>Mar\u00eda  Del Carmen Carre\u00f1o Garcia<\/li>\n<\/ul>\n<\/li>\n<li><strong>Tribunal<\/strong>\n<ul>\n<li>Presidente del tribunal: rafael Suau suarez <\/li>\n<li>nazario Martin leon (vocal)<\/li>\n<li>enrique Guiti\u00e1n rivera (vocal)<\/li>\n<li>Jos\u00e9 Perez sestelo (vocal)<\/li>\n<\/ul>\n<\/li>\n<\/ul>\n<p>&nbsp;<\/p>\n","protected":false},"excerpt":{"rendered":"<p>Tesis doctoral de Garc\u00eda Cerrada Susana M. 1,- se han establecido dos accesos complementarios a las dihidro[5]helicenoquinonas y bisquinonas enantiom\u00e9ricamente [&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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