Microwave-mediated intramolecular Diels-Alder cyclization of biodihydroxylated benzoic acid derivatives |
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Authors: | Marko D Mihovilovic Hannes G Leisch |
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Institution: | a Vienna University of Technology, Institute of Applied Synthetic Chemistry, Getreidemarkt 9/163-OC, A-1060 Vienna, Austria b Vienna University of Technology, Institute of Chemical Technology and Analytics, Getreidemarkt 9/164, A-1060 Vienna, Austria |
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Abstract: | The synthetic utility of biodihydroxylated benzoic acid derivatives for the construction of bridge bicyclo scaffolds was investigated. Biodihydroxylation of benzoic acid using Ralstonia eutropha B9 gave (1S,2R)-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylic acid (DCD) in high optical purity (>95% ee). Protection of the intermediate and subsequent functional group transformation gave the required cyclization precursors in moderate to excellent overall yields. Subsequent intramolecular Diels-Alder cyclization of biodihydroxylated benzoic acid derivatives was carried out using either thermal or microwave conditions. Enantiomerically pure products with five chiral centers were obtained in 4-6 steps from achiral starting material. |
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Keywords: | Biodihydroxylation Microwave chemistry Diels-Alder reaction Intramolecular cyclization Enantioselective synthesis |
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