Universität zu Köln

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:	Creators Email ORCID ORCID Put Code Kerl, Thomas UNSPECIFIED UNSPECIFIED UNSPECIFIED Berger, Florian UNSPECIFIED UNSPECIFIED UNSPECIFIED Schmalz, Hans-Guenther UNSPECIFIED orcid.org/0000-0003-0489-1827 UNSPECIFIED
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:	Keywords Language POTENT Multiple languages Chemistry, Multidisciplinary Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/28428