The reported enantioselective synthesis for the preparation of (+)-(2R,3R)-2-(4-
for the stereoselective synthesis of bioactive flavanolignans, could not be reproduced.
Thus, the target molecule was prepared via the synthesis and separation of diastereomeric
O-glucosides. TDDFT-ECD calculations and the 1,4-benzodioxane helicity rule were utilized
to determine the absolute configuration. ECD calculations also confirmed that the 1Lb
Cotton effect is governed by the helicity of the heteroring, while the higher-energy ECD
transitions reflect mainly the orientation of the equatorial C-2 aryl group.
Keywords: 1, 4-benzodioxane, flavanolignans, stereoselective synthesis, absolute configuration, TDDFT-ECD calculation, hydroxymethyl.
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