Evaluation of Different Synthetic Routes to (2R,3R)-3-Hydroxymethyl-2-(4-hydroxy- 3-methoxyphenyl)-1,4-Benzodioxane-6-Carbaldehyde

Author(s): Renáta Kertiné Ferenczi, Tünde-Zita Illyés, Sándor Balázs Király, Gyula Hoffka, László Szilágyi, Attila Mándi, Sándor Antus*, Tibor Kurtán*.

Journal Name: Current Organic Chemistry

Volume 23 , Issue 26 , 2019

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Abstract:

The reported enantioselective synthesis for the preparation of (+)-(2R,3R)-2-(4- hydroxy-3-methoxyphenyl)-3-hydroxymethyl-1,4-benzodioxane-6-carbaldehyde, precursor 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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Article Details

VOLUME: 23
ISSUE: 26
Year: 2019
Page: [2960 - 2968]
Pages: 9
DOI: 10.2174/1385272823666191212113407
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