{"id":2420,"date":"2018-06-04T16:33:54","date_gmt":"2018-06-04T16:33:54","guid":{"rendered":"https:\/\/www.sygnaturediscovery.com\/journal-paper\/diastereoselective-synthesis-of-highly-substituted-amino%e2%80%90-and-pyrrolidino%e2%80%90tetrahydrofurans-as-lead%e2%80%90like-molecular-scaffolds\/"},"modified":"2018-06-04T16:33:54","modified_gmt":"2018-06-04T16:33:54","slug":"diastereoselective-synthesis-of-highly-substituted-amino%e2%80%90-and-pyrrolidino%e2%80%90tetrahydrofurans-as-lead%e2%80%90like-molecular-scaffolds","status":"publish","type":"journal-paper","link":"https:\/\/www.sygnaturediscovery.com\/fr\/journal-paper\/diastereoselective-synthesis-of-highly-substituted-amino%e2%80%90-and-pyrrolidino%e2%80%90tetrahydrofurans-as-lead%e2%80%90like-molecular-scaffolds\/","title":{"rendered":"Diastereoselective Synthesis of Highly Substituted, Amino\u2010 and Pyrrolidino\u2010Tetrahydrofurans as Lead\u2010Like Molecular Scaffolds"},"content":{"rendered":"
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Authors: Dr. Steven M. Wales,\u00a0Dr. Elena G. Merisor\u00a0, Dr. Holly V. Adcock,\u00a0Dr. Christopher A. Pearce,\u00a0Dr. Ian R. Strutt,\u00a0Dr. William Lewis,\u00a0Dr. Daniel Hamza<\/i>\u00a0and Prof.\u2005Dr. Christopher J. Moody<\/span><\/div>\n
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First published:\u00a0<\/span>14 April 2018<\/span><\/span><\/div>\n
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https:\/\/doi.org\/10.1002\/chem.201801046<\/a><\/div>\n<\/div>\n<\/div>\n<\/div>\n
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Abstract<\/h3>\n
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A series of highly substituted tetrahydrofurans (THFs), decorated with modifiable 2\u2010aryl, 3\u2010carboxy and 4\u2010amino substituents, has been prepared for biological evaluation within the European Lead Factory. Diastereoselective reductive amination of pre\u2010functionalised 4\u2010oxofurans, readily prepared from cinnamate esters via oxa\u2010Michael\/Dieckmann annulation, provided the requisite THF cores on gram scale with three contiguous stereocentres, including full substitution at C\u20103. In a second series, a pyrrolidine ring was fused to the same oxofuran scaffold via an intramolecular reductive amination, inverting the configuration at C\u20104 relative to the other ring substituents. The resulting compounds, which displayed desirable physical properties as lead\u2010like scaffolds, were derivatised into a small library of 24\u2005compounds, demonstrating their ability to serve as starting points for drug discovery. Ultimately, this chemistry enabled the preparation of 1948 THF\u2010containing compounds for inclusion in the Joint European Compound Library.<\/p>\n<\/div>\n<\/div>\n

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