A new asymmetric synthesis of (+)-12b-epidevinylantirhine |
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| Authors: | Steven M Allin Jagjit S Khera Mark RJ Elsegood |
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| Institution: | a Department of Chemistry, Loughborough University, Loughborough, Leicestershire, LE11 3TU, UK
b Department of Medicinal Chemistry, Neurology and GI Centre of Excellence for Drug Discovery, GlaxoSmithKline Research Limited, New Frontiers Science Park, Third Avenue, Harlow, Essex, CM19 5AW, UK |
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| Abstract: | We report a new asymmetric synthesis of the indole alkaloid derivative (+)-12b-epidevinylantirhine through stereoselective cyclization of a tethered indole nucleus onto an N-acyliminium ion intermediate, generated from a readily available non-racemic bicyclic lactam building block, and subsequent template modification through a highly diastereoselective conjugate addition protocol. In addition, we present the first X-ray crystal structure of this indole target. |
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