{"id":2430,"date":"2018-11-19T11:23:55","date_gmt":"2018-11-19T11:23:55","guid":{"rendered":"https:\/\/www.sygnaturediscovery.com\/journal-paper\/synthesis-of-epibatidine-analogues-by-pyrrole-diels-alder-reactions-rapid-access-to-azabicyclo2-2-1heptane-and-38-diazabicyclo3-2-1octane-scaffolds-f\/"},"modified":"2018-11-19T11:23:55","modified_gmt":"2018-11-19T11:23:55","slug":"synthesis-of-epibatidine-analogues-by-pyrrole-diels-alder-reactions-rapid-access-to-azabicyclo2-2-1heptane-and-38-diazabicyclo3-2-1octane-scaffolds-f","status":"publish","type":"journal-paper","link":"https:\/\/www.sygnaturediscovery.com\/fr\/journal-paper\/synthesis-of-epibatidine-analogues-by-pyrrole-diels-alder-reactions-rapid-access-to-azabicyclo2-2-1heptane-and-38-diazabicyclo3-2-1octane-scaffolds-f\/","title":{"rendered":"Synthesis of Epibatidine Analogues by Pyrrole Diels-\u200bAlder Reactions: Rapid Access to Azabicyclo[2.2.1]\u200bheptane and 3,\u200b8-\u200bDiazabicyclo[3.2.1]\u200boctane Scaffolds for Library Synthesis"},"content":{"rendered":"<p>Alexander T. Murray, Emma Packard, Andrew Nortcliffe, William Lewis, Daniel Hamza, Geraint Jones, Christopher J. Moody<\/p>\n<p><strong>Abstract<\/strong><\/p>\n<p>Analogues of the nicotinic acetylcholine antagonist epibatidine, suitable for diversification, were synthesized by application of a pyrrole Diels\u2013Alder strategy, allowing rapid generation of azabicyclo[2.2.1]heptane bicyclic cores. Further molecular complexity could be accessed by using intramolecular Diels\u2013Alder reactions, or ring expansion by ozonolysis\u2013reductive amination chemistry. Scaffolds were designed such that they could be orthogonally deprotected, yielding three points of diversity for library synthesis, exemplified by 24 compounds synthesized from four cores.<\/p>\n<p><strong>Ref:<\/strong>\u00a0European Journal of Organic Chemistry\u00a0(2017),\u00a02017(1),\u00a0138-148<\/p>\n","protected":false},"excerpt":{"rendered":"","protected":false},"featured_media":0,"template":"","category":[1],"resource_tag":[],"class_list":["post-2430","journal-paper","type-journal-paper","status-publish","hentry","category-uncategorized"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v28.7 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Epibatidine Analogs by Pyrrole Diels\u2013Alder Reactions<\/title>\n<meta name=\"description\" content=\"This journal paper describes a pyrrole Diels\u2013Alder strategy for rapid synthesis of epibatidine analogs and diversifiable bicyclic scaffolds. 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