Synthesis of Natural Rubrolides B, I, K, L, M, O and Analogues

Autor:	Wolfgang R. Streit, Stephanie Stanelle-Bertram, Nina Schützenmeister, Jessica de Vries, Judith Krauß, Mirja Gudzuhn, Jasmin Janneschütz, Gülsah Gabriel, Maik Assmann
Rok vydání:	2021
Předmět:	Natural products Halogenation Chemistry Stereochemistry Organic Chemistry Total synthesis medicine.disease_cause Rubrolides Antiviral agents Influenza A virus medicine Aldol condensation Physical and Theoretical Chemistry Tetronic acid
Zdroj:	European Journal of Organic Chemistry. 2021:4195-4200
ISSN:	1099-0690 1434-193X
DOI:	10.1002/ejoc.202100526
Popis:	The chlorinated natural products, rubrolides B, I, K, L, M and O and analogues were synthesized in only five steps employing a robust and divergent synthetic strategy. The synthesis is performed without using protecting groups starting from a key intermediate, which can be synthesized from commercially available tetronic acid in only two steps. Selective halogenation and vinylogous aldol condensation enable the efficient synthesis of highly halogenated natural occurring rubrolides as well as synthetic analogues to build up a compound library for antiviral and antibiofilm testing. All synthesized compounds were then tested for their activity against the two influenza A virus strains pH1N1 and H3N2 as well as for their antibiofilm activity. Naturally occurring as well as synthetic analogues showed promising antiviral and antibiofilm activities.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::41de9ffb4b148b0c1096a52612f73a02 https://doi.org/10.1002/ejoc.202100526 Zobrazit plný text záznamu Plný text ve formátu PDF