Kerl, Thomas, Berger, Florian and Schmalz, Hans-Guenther ORCID: 0000-0003-0489-1827 (2016). Total Synthesis of the Antiviral Natural Product Houttuynoid B. Chem.-Eur. J., 22 (9). S. 2935 - 2939. WEINHEIM: WILEY-V C H VERLAG GMBH. ISSN 1521-3765

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Abstract

The first total synthesis of houttuynoid B, a powerful antiviral flavonoid glycoside from the Chinese plant Houttuynia cordata, is described. In a key step, a Baker-Venkataraman rearrangement employing an already glycosylated substrate was used to efficiently set up the fully functionalized carbon skeleton. The required benzofuran building block was prepared through a domino Sonogashira coupling/5-endo-dig cyclization and converted into a stable 1-hydroxybenzotriazole-derived active ester prior to linking with a galactosylated hydroxyacetophenone unit. The elaborated synthesis requires only nine steps (11% overall yield) along the longest linear sequence and paves the way for the preparation of structurally related compounds for further biological evaluation.

Item Type: Journal Article
Creators:
CreatorsEmailORCIDORCID Put Code
Kerl, ThomasUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Berger, FlorianUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Schmalz, Hans-GuentherUNSPECIFIEDorcid.org/0000-0003-0489-1827UNSPECIFIED
URN: urn:nbn:de:hbz:38-284287
DOI: 10.1002/chem.201505118
Journal or Publication Title: Chem.-Eur. J.
Volume: 22
Number: 9
Page Range: S. 2935 - 2939
Date: 2016
Publisher: WILEY-V C H VERLAG GMBH
Place of Publication: WEINHEIM
ISSN: 1521-3765
Language: English
Faculty: Faculty of Mathematics and Natural Sciences
Divisions: Faculty of Mathematics and Natural Sciences > Department of Chemistry > Institute of Organic Chemistry
Subjects: no entry
Uncontrolled Keywords:
KeywordsLanguage
POTENTMultiple languages
Chemistry, MultidisciplinaryMultiple languages
Refereed: Yes
URI: http://kups.ub.uni-koeln.de/id/eprint/28428

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