{"id":473,"date":"2017-06-27T03:55:14","date_gmt":"2017-06-27T03:55:14","guid":{"rendered":"http:\/\/localhost\/skpresearch\/?p=228"},"modified":"2017-06-27T03:55:14","modified_gmt":"2017-06-27T03:55:14","slug":"santonic-acid-zn-hcl-ether-reduction-and-ceric-ammonium-nitrate-oxidation","status":"publish","type":"post","link":"https:\/\/skpresearch.org\/?p=473","title":{"rendered":"Santonic acid: Zn \u2013HCl \u2013 ether reduction and ceric ammonium nitrate oxidation"},"content":{"rendered":"\t\t<div data-elementor-type=\"wp-post\" data-elementor-id=\"473\" class=\"elementor elementor-473\" data-elementor-post-type=\"post\">\n\t\t\t\t\t\t<section class=\"elementor-section elementor-top-section elementor-element elementor-element-24d879d elementor-section-boxed elementor-section-height-default elementor-section-height-default\" data-id=\"24d879d\" data-element_type=\"section\">\n\t\t\t\t\t\t<div class=\"elementor-container elementor-column-gap-default\">\n\t\t\t\t\t<div class=\"elementor-column elementor-col-100 elementor-top-column elementor-element elementor-element-9532646\" data-id=\"9532646\" data-element_type=\"column\">\n\t\t\t<div class=\"elementor-widget-wrap elementor-element-populated\">\n\t\t\t\t\t\t<div class=\"elementor-element elementor-element-ce6ffcb elementor-widget elementor-widget-text-editor\" data-id=\"ce6ffcb\" data-element_type=\"widget\" data-widget_type=\"text-editor.default\">\n\t\t\t\t<div class=\"elementor-widget-container\">\n\t\t\t\t\t\t\t\t\t<p><b>1. Introduction<\/b><br>(2 )-a-Santonin (1, Figure 1), a naturally occurring sesquiterpene lactone, is an attractive starting material for the synthesis of several natural products, transformational studies and stereochemical correlations (Paknikar et al. 1994; Furtado et al. 1998; Blay et al. 2004; Natarajan et al. 2007; Arantes et al. 2009; Lamm et al. 2009; Li et al. 2010). (2 )-Santonic acid (2, Figure 1), easily accessible in a single step from (2 )-a-santonin (Birladeanu 2003) has, however, been explored to a very limited extent (Hortmann et al. 1968; Hortmann &amp; Daniel 1972; Naik et al. 1987; Moyano et al. 2005; Williams et al. 2008). (2 )-Santonic acid (2) appears<br>to be a good precursor for bicyclic skeletons present among natural products. An aim of this work was to seek entry into bicyclo[3.3.0]octane systems using Zn \u2013HCl \u2013 ether reduction (Toda et al. 1972) to obtain pinacol (3) (Figure 1) followed by acid-catalysed molecular rearrangement. Entry into bicyclo[4.3.0]nonane skeleton has been reported (Hortmann &amp; Daniel 1972; Naik et al. 1987), and it was our interest to explore an alternate entry into this skeleton via oxidation of 2 with ceric ammonium nitrate (CAN).<\/p><p>To read the full publication download the following pdf Natural Products Research &#8211; Sanatonic acid<\/p>\t\t\t\t\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t\t<\/div>\n\t\t<\/div>\n\t\t\t\t\t<\/div>\n\t\t<\/section>\n\t\t\t\t<\/div>\n\t\t","protected":false},"excerpt":{"rendered":"<p>1. Introduction(2 )-a-Santonin (1, Figure 1), a naturally occurring sesquiterpene lactone, is an attractive starting material for the synthesis of [&hellip;]<\/p>\n","protected":false},"author":1,"featured_media":229,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"inline_featured_image":false,"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-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-opacity":"","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-opacity":"","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-opacity":"","overlay-gradient":""}},"ast-content-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-opacity":"","overlay-gradient":""},"tablet":{"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-opacity":"","overlay-gradient":""},"mobile":{"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-opacity":"","overlay-gradient":""}},"footnotes":""},"categories":[2],"tags":[],"class_list":["post-473","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-blog-post"],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v25.3 - https:\/\/yoast.com\/wordpress\/plugins\/seo\/ -->\n<title>Santonic acid: Zn \u2013HCl \u2013 ether reduction and ceric ammonium nitrate oxidation - Prof. S K Paknikar<\/title>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/skpresearch.org\/?p=473\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Santonic acid: Zn \u2013HCl \u2013 ether reduction and ceric ammonium nitrate oxidation - Prof. S K Paknikar\" \/>\n<meta property=\"og:description\" content=\"1. Introduction(2 )-a-Santonin (1, Figure 1), a naturally occurring sesquiterpene lactone, is an attractive starting material for the synthesis of [&hellip;]\" \/>\n<meta property=\"og:url\" content=\"https:\/\/skpresearch.org\/?p=473\" \/>\n<meta property=\"og:site_name\" content=\"Prof. S K Paknikar\" \/>\n<meta property=\"article:published_time\" content=\"2017-06-27T03:55:14+00:00\" \/>\n<meta property=\"og:image\" content=\"https:\/\/skpresearch.org\/wp-content\/uploads\/2021\/03\/F24-150x150.png\" \/>\n\t<meta property=\"og:image:width\" content=\"150\" \/>\n\t<meta property=\"og:image:height\" content=\"150\" \/>\n\t<meta property=\"og:image:type\" content=\"image\/png\" \/>\n<meta name=\"author\" content=\"admin\" \/>\n<meta name=\"twitter:card\" content=\"summary_large_image\" \/>\n<meta name=\"twitter:label1\" content=\"Written by\" \/>\n\t<meta name=\"twitter:data1\" content=\"admin\" \/>\n\t<meta name=\"twitter:label2\" content=\"Est. reading time\" \/>\n\t<meta name=\"twitter:data2\" content=\"1 minute\" \/>\n<script type=\"application\/ld+json\" class=\"yoast-schema-graph\">{\"@context\":\"https:\/\/schema.org\",\"@graph\":[{\"@type\":\"WebPage\",\"@id\":\"https:\/\/skpresearch.org\/?p=473\",\"url\":\"https:\/\/skpresearch.org\/?p=473\",\"name\":\"Santonic acid: Zn \u2013HCl \u2013 ether reduction and ceric ammonium nitrate oxidation - Prof. S K Paknikar\",\"isPartOf\":{\"@id\":\"https:\/\/skpresearch.org\/#website\"},\"primaryImageOfPage\":{\"@id\":\"https:\/\/skpresearch.org\/?p=473#primaryimage\"},\"image\":{\"@id\":\"https:\/\/skpresearch.org\/?p=473#primaryimage\"},\"thumbnailUrl\":\"https:\/\/skpresearch.org\/wp-content\/uploads\/2021\/03\/F24-150x150.png\",\"datePublished\":\"2017-06-27T03:55:14+00:00\",\"author\":{\"@id\":\"https:\/\/skpresearch.org\/#\/schema\/person\/d561f8d9d32002b11c19ea52b06dfe84\"},\"breadcrumb\":{\"@id\":\"https:\/\/skpresearch.org\/?p=473#breadcrumb\"},\"inLanguage\":\"en-US\",\"potentialAction\":[{\"@type\":\"ReadAction\",\"target\":[\"https:\/\/skpresearch.org\/?p=473\"]}]},{\"@type\":\"ImageObject\",\"inLanguage\":\"en-US\",\"@id\":\"https:\/\/skpresearch.org\/?p=473#primaryimage\",\"url\":\"https:\/\/skpresearch.org\/wp-content\/uploads\/2021\/03\/F24-150x150.png\",\"contentUrl\":\"https:\/\/skpresearch.org\/wp-content\/uploads\/2021\/03\/F24-150x150.png\",\"width\":150,\"height\":150},{\"@type\":\"BreadcrumbList\",\"@id\":\"https:\/\/skpresearch.org\/?p=473#breadcrumb\",\"itemListElement\":[{\"@type\":\"ListItem\",\"position\":1,\"name\":\"Home\",\"item\":\"https:\/\/skpresearch.org\/\"},{\"@type\":\"ListItem\",\"position\":2,\"name\":\"Santonic acid: Zn \u2013HCl \u2013 ether reduction and ceric ammonium nitrate oxidation\"}]},{\"@type\":\"WebSite\",\"@id\":\"https:\/\/skpresearch.org\/#website\",\"url\":\"https:\/\/skpresearch.org\/\",\"name\":\"Prof. S k Paknikar\",\"description\":\"Welcome to the official website of Prof. Shashikumar K. Paknikar, a veteran chemist with over 69 years in research, specializing in natural product chemistry, clay catalysis, and academic mentorship.\",\"potentialAction\":[{\"@type\":\"SearchAction\",\"target\":{\"@type\":\"EntryPoint\",\"urlTemplate\":\"https:\/\/skpresearch.org\/?s={search_term_string}\"},\"query-input\":{\"@type\":\"PropertyValueSpecification\",\"valueRequired\":true,\"valueName\":\"search_term_string\"}}],\"inLanguage\":\"en-US\"},{\"@type\":\"Person\",\"@id\":\"https:\/\/skpresearch.org\/#\/schema\/person\/d561f8d9d32002b11c19ea52b06dfe84\",\"name\":\"admin\",\"image\":{\"@type\":\"ImageObject\",\"inLanguage\":\"en-US\",\"@id\":\"https:\/\/skpresearch.org\/#\/schema\/person\/image\/\",\"url\":\"https:\/\/secure.gravatar.com\/avatar\/2dfbf55776bfad528e720b811012ad2118246b23a5551c5f4942f3a90a5fb665?s=96&d=mm&r=g\",\"contentUrl\":\"https:\/\/secure.gravatar.com\/avatar\/2dfbf55776bfad528e720b811012ad2118246b23a5551c5f4942f3a90a5fb665?s=96&d=mm&r=g\",\"caption\":\"admin\"},\"sameAs\":[\"https:\/\/skpresearch.org\"],\"url\":\"https:\/\/skpresearch.org\/?author=1\"}]}<\/script>\n<!-- \/ Yoast SEO plugin. -->","yoast_head_json":{"title":"Santonic acid: Zn \u2013HCl \u2013 ether reduction and ceric ammonium nitrate oxidation - Prof. S K Paknikar","robots":{"index":"index","follow":"follow","max-snippet":"max-snippet:-1","max-image-preview":"max-image-preview:large","max-video-preview":"max-video-preview:-1"},"canonical":"https:\/\/skpresearch.org\/?p=473","og_locale":"en_US","og_type":"article","og_title":"Santonic acid: Zn \u2013HCl \u2013 ether reduction and ceric ammonium nitrate oxidation - Prof. S K Paknikar","og_description":"1. Introduction(2 )-a-Santonin (1, Figure 1), a naturally occurring sesquiterpene lactone, is an attractive starting material for the synthesis of [&hellip;]","og_url":"https:\/\/skpresearch.org\/?p=473","og_site_name":"Prof. S K Paknikar","article_published_time":"2017-06-27T03:55:14+00:00","og_image":[{"width":150,"height":150,"url":"https:\/\/skpresearch.org\/wp-content\/uploads\/2021\/03\/F24-150x150.png","type":"image\/png"}],"author":"admin","twitter_card":"summary_large_image","twitter_misc":{"Written by":"admin","Est. reading time":"1 minute"},"schema":{"@context":"https:\/\/schema.org","@graph":[{"@type":"WebPage","@id":"https:\/\/skpresearch.org\/?p=473","url":"https:\/\/skpresearch.org\/?p=473","name":"Santonic acid: Zn \u2013HCl \u2013 ether reduction and ceric ammonium nitrate oxidation - Prof. S K Paknikar","isPartOf":{"@id":"https:\/\/skpresearch.org\/#website"},"primaryImageOfPage":{"@id":"https:\/\/skpresearch.org\/?p=473#primaryimage"},"image":{"@id":"https:\/\/skpresearch.org\/?p=473#primaryimage"},"thumbnailUrl":"https:\/\/skpresearch.org\/wp-content\/uploads\/2021\/03\/F24-150x150.png","datePublished":"2017-06-27T03:55:14+00:00","author":{"@id":"https:\/\/skpresearch.org\/#\/schema\/person\/d561f8d9d32002b11c19ea52b06dfe84"},"breadcrumb":{"@id":"https:\/\/skpresearch.org\/?p=473#breadcrumb"},"inLanguage":"en-US","potentialAction":[{"@type":"ReadAction","target":["https:\/\/skpresearch.org\/?p=473"]}]},{"@type":"ImageObject","inLanguage":"en-US","@id":"https:\/\/skpresearch.org\/?p=473#primaryimage","url":"https:\/\/skpresearch.org\/wp-content\/uploads\/2021\/03\/F24-150x150.png","contentUrl":"https:\/\/skpresearch.org\/wp-content\/uploads\/2021\/03\/F24-150x150.png","width":150,"height":150},{"@type":"BreadcrumbList","@id":"https:\/\/skpresearch.org\/?p=473#breadcrumb","itemListElement":[{"@type":"ListItem","position":1,"name":"Home","item":"https:\/\/skpresearch.org\/"},{"@type":"ListItem","position":2,"name":"Santonic acid: Zn \u2013HCl \u2013 ether reduction and ceric ammonium nitrate oxidation"}]},{"@type":"WebSite","@id":"https:\/\/skpresearch.org\/#website","url":"https:\/\/skpresearch.org\/","name":"Prof. S k Paknikar","description":"Welcome to the official website of Prof. Shashikumar K. Paknikar, a veteran chemist with over 69 years in research, specializing in natural product chemistry, clay catalysis, and academic mentorship.","potentialAction":[{"@type":"SearchAction","target":{"@type":"EntryPoint","urlTemplate":"https:\/\/skpresearch.org\/?s={search_term_string}"},"query-input":{"@type":"PropertyValueSpecification","valueRequired":true,"valueName":"search_term_string"}}],"inLanguage":"en-US"},{"@type":"Person","@id":"https:\/\/skpresearch.org\/#\/schema\/person\/d561f8d9d32002b11c19ea52b06dfe84","name":"admin","image":{"@type":"ImageObject","inLanguage":"en-US","@id":"https:\/\/skpresearch.org\/#\/schema\/person\/image\/","url":"https:\/\/secure.gravatar.com\/avatar\/2dfbf55776bfad528e720b811012ad2118246b23a5551c5f4942f3a90a5fb665?s=96&d=mm&r=g","contentUrl":"https:\/\/secure.gravatar.com\/avatar\/2dfbf55776bfad528e720b811012ad2118246b23a5551c5f4942f3a90a5fb665?s=96&d=mm&r=g","caption":"admin"},"sameAs":["https:\/\/skpresearch.org"],"url":"https:\/\/skpresearch.org\/?author=1"}]}},"_links":{"self":[{"href":"https:\/\/skpresearch.org\/index.php?rest_route=\/wp\/v2\/posts\/473","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/skpresearch.org\/index.php?rest_route=\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/skpresearch.org\/index.php?rest_route=\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/skpresearch.org\/index.php?rest_route=\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/skpresearch.org\/index.php?rest_route=%2Fwp%2Fv2%2Fcomments&post=473"}],"version-history":[{"count":0,"href":"https:\/\/skpresearch.org\/index.php?rest_route=\/wp\/v2\/posts\/473\/revisions"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/skpresearch.org\/index.php?rest_route=\/wp\/v2\/media\/229"}],"wp:attachment":[{"href":"https:\/\/skpresearch.org\/index.php?rest_route=%2Fwp%2Fv2%2Fmedia&parent=473"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/skpresearch.org\/index.php?rest_route=%2Fwp%2Fv2%2Fcategories&post=473"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/skpresearch.org\/index.php?rest_route=%2Fwp%2Fv2%2Ftags&post=473"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}