Journal
ORGANIC LETTERS
Volume 19, Issue 5, Pages 1156-1159Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b00194
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Funding
- Natural Sciences and Engineering Research Council of Canada (NSERC)
- Canada Research Chair Program
- Canada Foundation for Innovation (CFI)
- TDC Research, Inc
- TDC Research Foundation
- Ontario Partnership for Innovation and Commercialization (OPIC)
- The Advanced Biomanufacturing Centre (Brock University)
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The hydroxylated cyclohexenone carboxylic acid moiety of xylosmin was synthesized in eight steps from benzoic acid. The key steps in the synthesis involved the enzymatic dihydroxylation of benzoic acid by the whole cell fermentation with Ralstonia eutrophus B9, and Henbest epoxidation. Early attempts led to the synthesis of a C6 epimer of the methyl ester of the hydroxylated cyclohexenone carboxylic acid moiety. The absolute stereochemistry of an advanced intermediate was confirmed by X-ray crystallography. Complete characterization of the previously reported but not fully characterized hydroxylated cyclohexenone carboxylic acid is provided.
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