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Asymmetric Synthesis of Natural and Unnatural Dibenzylbutane Lignans from a Common Intermediate
Daniel E Jeffries1, Craig W Lindsley1
1Departments of Pharmacology and Chemistry, Vanderbilt Center for Neuroscience Drug Discovery , Vanderbilt University , Nashville , Tennessee 37232 , United States.
Abstract:
Lignans are a structurally diverse class of natural products with extensive pharmacological effects. Here we report the syntheses of both natural and unnatural dibenzylbutane lignans from a common intermediate, which is prepared in five steps from known materials. Derivatization of this intermediate affords lignans featuring contiguous stereocenters in a high diastereomeric purity after chromatography. This divergent synthetic route can be exploited to prepare dibenzylbutane lignans and analogues thereof to probe their biological profiles.
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