Movahhed, Sohajl, Westphal, Julia, Kempa, Alexander, Schumacher, Christian Eric, Sperlich, Julia, Neudoerfl, Jorg-Martin, Teusch, Nicole, Hochguertel, Matthias and Schmalz, Hans-Guenther ORCID: 0000-0003-0489-1827 (2021). Total Synthesis of (+)-Erogorgiaene and the Pseudopterosin A-F Aglycone via Enantioselective Cobalt-Catalyzed Hydrovinylation. Chem.-Eur. J., 27 (45). S. 11574 - 11580. WEINHEIM: WILEY-V C H VERLAG GMBH. ISSN 1521-3765

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Abstract

Due to their pronounced bioactivity and limited availability from natural resources, metabolites of the soft coral Pseudopterogorgia elisabethae, such as erogorgiaene and the pseudopterosines, represent important target molecules for chemical synthesis. We have now developed a particularly short and efficient route towards these marine diterpenes exploiting an operationally convenient enantioselective cobalt-catalyzed hydrovinylation as the chirogenic step. Other noteworthy C-C bond forming transformations include diastereoselective Lewis acid-mediated cyclizations, a Suzuki coupling and a carbonyl ene reaction. Starting from 4-methyl-styrene the anti-tubercular agent (+)-erogorgiaene (>98 % ee) was prepared in only 7 steps with 46 % overall yield. In addition, the synthesis of the pseudopterosin A aglycone was achieved in 12 steps with 30 % overall yield and, surprisingly, was found to exhibit a similar anti-inflammatory activity (inhibition of LPS-induced NF-kappa B activation) as a natural mixture of pseudopterosins A-D or iso-pseudopterosin A, prepared by beta-D-xylosylation of the synthetic aglycone.

Item Type: Journal Article
Creators:
CreatorsEmailORCIDORCID Put Code
Movahhed, SohajlUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Westphal, JuliaUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Kempa, AlexanderUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Schumacher, Christian EricUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Sperlich, JuliaUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Neudoerfl, Jorg-MartinUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Teusch, NicoleUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Hochguertel, MatthiasUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Schmalz, Hans-GuentherUNSPECIFIEDorcid.org/0000-0003-0489-1827UNSPECIFIED
URN: urn:nbn:de:hbz:38-568892
DOI: 10.1002/chem.202101863
Journal or Publication Title: Chem.-Eur. J.
Volume: 27
Number: 45
Page Range: S. 11574 - 11580
Date: 2021
Publisher: WILEY-V C H VERLAG GMBH
Place of Publication: WEINHEIM
ISSN: 1521-3765
Language: English
Faculty: Unspecified
Divisions: Unspecified
Subjects: no entry
Uncontrolled Keywords:
KeywordsLanguage
ENANTIOSPECIFIC TOTAL-SYNTHESIS; SECO-PSEUDOPTEROSINS; NATURAL-PRODUCTS; DITERPENE-GLYCOSIDES; SAN ANDRES; ELISABETHAE; ROUTE; SEA; CONJUGATE; OCTOCORALMultiple languages
Chemistry, MultidisciplinaryMultiple languages
URI: http://kups.ub.uni-koeln.de/id/eprint/56889

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