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

Ferenczi, Renáta and Illyés, Tünde Zita and Király, Sándor Balázs and Hoffka, Gyula and Szilágyi, László and Mándi, Attila and Antus, Sándor and Kurtán, Tibor (2019) Evaluation of Different Synthetic Routes to (2R,3R)-3-Hydroxymethyl-2-(4-hydroxy-3-methoxyphenyl)-1,4-Benzodioxane-6-Carbaldehyde. Current Organic Chemistry, 23 (26). pp. 2960-2968. ISSN 1875-5348

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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.

Item Type: Article
Subjects: Q Science / természettudomány > QD Chemistry / kémia > QD01 Analytical chemistry / analitikai kémia
Q Science / természettudomány > QD Chemistry / kémia > QD04 Organic chemistry / szerves kémia
Depositing User: Mándi Attila
Date Deposited: 23 Sep 2020 09:22
Last Modified: 23 Sep 2020 09:22

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