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

Text CurrOrgChem_2019_23_2960_FerencziR.pdf Restricted to Registered users only Download (1MB)

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.

Actions (login required)

Edit Item