{"id":27,"date":"2017-02-09T10:34:57","date_gmt":"2017-02-09T15:34:57","guid":{"rendered":"https:\/\/sciencescosmaincms.cm.ucf.edu\/chemistry\/yuanlab\/?page_id=27"},"modified":"2017-02-09T13:59:06","modified_gmt":"2017-02-09T18:59:06","slug":"research","status":"publish","type":"page","link":"https:\/\/sciences.ucf.edu\/chemistry\/yuanlab\/research\/","title":{"rendered":"Research Interest"},"content":{"rendered":"<p>An asymmetric synthesis of carbocyclic spiroindoline by sequential Michael reaction and [3+2]-cycloaddition was achieved in our laboratories. This protocol demonstrates excellent enantio- and diastereoselectivity with broad functional group tolerance. A diverse range of spiroindolines were prepared by this approach and the products served as ideal substrates for C2 derivatization.<\/p>\n<p><img decoding=\"async\" class=\"alignnone size-full wp-image-28 lazyload\" data-src=\"https:\/\/sciences.ucf.edu\/chemistry\/yuanlab\/wp-content\/uploads\/sites\/2\/sites\/23\/2017\/02\/research1.jpg\" alt=\"\" width=\"490\" height=\"662\" data-srcset=\"https:\/\/sciences.ucf.edu\/chemistry\/yuanlab\/wp-content\/uploads\/sites\/23\/2017\/02\/research1.jpg 490w, https:\/\/sciences.ucf.edu\/chemistry\/yuanlab\/wp-content\/uploads\/sites\/23\/2017\/02\/research1-222x300.jpg 222w\" data-sizes=\"(max-width: 490px) 100vw, 490px\" src=\"data:image\/svg+xml;base64,PHN2ZyB3aWR0aD0iMSIgaGVpZ2h0PSIxIiB4bWxucz0iaHR0cDovL3d3dy53My5vcmcvMjAwMC9zdmciPjwvc3ZnPg==\" style=\"--smush-placeholder-width: 490px; --smush-placeholder-aspect-ratio: 490\/662;\" \/><\/p>\n<p>A highly stereoselective and scalable synthesis of\u00a0l-allo-enduracididine from hydroxyproline derivative was recently disclosed by us. Pyrrolidine oxidation and reductive ring opening are the key steps in the synthesis. Compared to previously reported approaches, current route affords\u00a0l-allo-enduracididine in 10 steps from\u00a0Boc-<em>trans<\/em>-Hyp-O<em>t<\/em>Bu in 31% overall yield with &gt;50:1 diastereoselectivity.<\/p>\n<p><img decoding=\"async\" class=\"alignnone size-full wp-image-29 lazyload\" data-src=\"https:\/\/sciences.ucf.edu\/chemistry\/yuanlab\/wp-content\/uploads\/sites\/2\/sites\/23\/2017\/02\/research2.jpg\" alt=\"\" width=\"454\" height=\"586\" data-srcset=\"https:\/\/sciences.ucf.edu\/chemistry\/yuanlab\/wp-content\/uploads\/sites\/23\/2017\/02\/research2.jpg 454w, https:\/\/sciences.ucf.edu\/chemistry\/yuanlab\/wp-content\/uploads\/sites\/23\/2017\/02\/research2-232x300.jpg 232w\" data-sizes=\"(max-width: 454px) 100vw, 454px\" src=\"data:image\/svg+xml;base64,PHN2ZyB3aWR0aD0iMSIgaGVpZ2h0PSIxIiB4bWxucz0iaHR0cDovL3d3dy53My5vcmcvMjAwMC9zdmciPjwvc3ZnPg==\" style=\"--smush-placeholder-width: 454px; --smush-placeholder-aspect-ratio: 454\/586;\" \/><\/p>\n<p>&nbsp;<\/p>\n","protected":false},"excerpt":{"rendered":"<p>An asymmetric synthesis of carbocyclic spiroindoline by sequential Michael reaction and [3+2]-cycloaddition was achieved in our laboratories. This protocol demonstrates&hellip;<\/p>\n","protected":false},"author":3,"featured_media":86,"parent":0,"menu_order":0,"comment_status":"closed","ping_status":"closed","template":"","meta":{"footnotes":"","_links_to":"","_links_to_target":""},"class_list":["post-27","page","type-page","status-publish","has-post-thumbnail","hentry"],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.2 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Research Interest - The Yuan Lab<\/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:\/\/sciences.ucf.edu\/chemistry\/yuanlab\/research\/\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Research Interest - The Yuan Lab\" \/>\n<meta property=\"og:description\" content=\"An asymmetric synthesis of carbocyclic spiroindoline by sequential Michael reaction and [3+2]-cycloaddition was achieved in our laboratories. This protocol demonstrates&hellip;\" \/>\n<meta property=\"og:url\" content=\"https:\/\/sciences.ucf.edu\/chemistry\/yuanlab\/research\/\" \/>\n<meta property=\"og:site_name\" content=\"The Yuan Lab\" \/>\n<meta property=\"article:modified_time\" content=\"2017-02-09T18:59:06+00:00\" \/>\n<meta property=\"og:image\" content=\"https:\/\/sciences.ucf.edu\/chemistry\/yuanlab\/wp-content\/uploads\/sites\/23\/2017\/02\/ptblocksucftype.jpg\" \/>\n\t<meta property=\"og:image:width\" content=\"1180\" \/>\n\t<meta property=\"og:image:height\" content=\"300\" \/>\n\t<meta property=\"og:image:type\" content=\"image\/jpeg\" \/>\n<meta name=\"twitter:card\" content=\"summary_large_image\" \/>\n<script type=\"application\/ld+json\" class=\"yoast-schema-graph\">{\"@context\":\"https:\/\/schema.org\",\"@graph\":[{\"@type\":\"WebPage\",\"@id\":\"https:\/\/sciences.ucf.edu\/chemistry\/yuanlab\/research\/\",\"url\":\"https:\/\/sciences.ucf.edu\/chemistry\/yuanlab\/research\/\",\"name\":\"Research Interest - The Yuan Lab\",\"isPartOf\":{\"@id\":\"https:\/\/sciences.ucf.edu\/chemistry\/yuanlab\/#website\"},\"primaryImageOfPage\":{\"@id\":\"https:\/\/sciences.ucf.edu\/chemistry\/yuanlab\/research\/#primaryimage\"},\"image\":{\"@id\":\"https:\/\/sciences.ucf.edu\/chemistry\/yuanlab\/research\/#primaryimage\"},\"thumbnailUrl\":\"https:\/\/sciences.ucf.edu\/chemistry\/yuanlab\/wp-content\/uploads\/sites\/23\/2017\/02\/ptblocksucftype.jpg\",\"datePublished\":\"2017-02-09T15:34:57+00:00\",\"dateModified\":\"2017-02-09T18:59:06+00:00\",\"inLanguage\":\"en-US\",\"potentialAction\":[{\"@type\":\"ReadAction\",\"target\":[\"https:\/\/sciences.ucf.edu\/chemistry\/yuanlab\/research\/\"]}]},{\"@type\":\"ImageObject\",\"inLanguage\":\"en-US\",\"@id\":\"https:\/\/sciences.ucf.edu\/chemistry\/yuanlab\/research\/#primaryimage\",\"url\":\"https:\/\/sciences.ucf.edu\/chemistry\/yuanlab\/wp-content\/uploads\/sites\/23\/2017\/02\/ptblocksucftype.jpg\",\"contentUrl\":\"https:\/\/sciences.ucf.edu\/chemistry\/yuanlab\/wp-content\/uploads\/sites\/23\/2017\/02\/ptblocksucftype.jpg\",\"width\":1180,\"height\":300,\"caption\":\"Wooden blocks displaying the symbols for Uranium (U), Carbon (C), and Fluorine (F) from the periodic table against a light blue background.\"},{\"@type\":\"WebSite\",\"@id\":\"https:\/\/sciences.ucf.edu\/chemistry\/yuanlab\/#website\",\"url\":\"https:\/\/sciences.ucf.edu\/chemistry\/yuanlab\/\",\"name\":\"The Yuan Lab\",\"description\":\"Department of Chemistry, University of Central Florida\",\"potentialAction\":[{\"@type\":\"SearchAction\",\"target\":{\"@type\":\"EntryPoint\",\"urlTemplate\":\"https:\/\/sciences.ucf.edu\/chemistry\/yuanlab\/?s={search_term_string}\"},\"query-input\":{\"@type\":\"PropertyValueSpecification\",\"valueRequired\":true,\"valueName\":\"search_term_string\"}}],\"inLanguage\":\"en-US\"}]}<\/script>\n<!-- \/ Yoast SEO plugin. -->","yoast_head_json":{"title":"Research Interest - The Yuan Lab","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:\/\/sciences.ucf.edu\/chemistry\/yuanlab\/research\/","og_locale":"en_US","og_type":"article","og_title":"Research Interest - The Yuan Lab","og_description":"An asymmetric synthesis of carbocyclic spiroindoline by sequential Michael reaction and [3+2]-cycloaddition was achieved in our laboratories. 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