2.50
Hdl Handle:
http://hdl.handle.net/10033/620829
Title:
A selective 3-acylation of tetramic acids and the first synthesis of ravenic acid.
Authors:
Schlenk, Andrea; Diestel, Randi; Sasse, Florenz; Schobert, Rainer
Abstract:
3-Acyltetramic acids, including delicate 3-oligoenoyl derivatives, such as the Penicillium metabolite ravenic acid, were prepared in two high-yielding steps. Reaction of tetramic acids with the ylide Ph(3)PCCO afforded exclusively the corresponding 3-acylylidenetetramic acids. These were amenable to Wittig olefinations with aliphatic, aromatic, saturated and unsaturated aldehydes after deprotonation with KOtBu. Due to its simplicity, selectivity and tolerance of pH-sensitive groups this method is superior to the established acylation protocols by Jones and Yoshii. It is also applicable to the synthesis of 3-acyltetronic acids. The new 3-oligoenoyl tetramic acids exhibited structure-dependent antimicrobial and cytotoxic activity.
Affiliation:
Helmholtz Centre for infection research, Inhoffenstr. 7, 38124 Braunschweig, Germany.
Citation:
A selective 3-acylation of tetramic acids and the first synthesis of ravenic acid. 2010, 16 (8):2599-604 Chemistry
Journal:
Chemistry (Weinheim an der Bergstrasse, Germany)
Issue Date:
22-Feb-2010
URI:
http://hdl.handle.net/10033/620829
DOI:
10.1002/chem.200902544
PubMed ID:
20066698
Type:
Article
Language:
en
ISSN:
1521-3765
Appears in Collections:
Publications of the research group Chemical Biology (CBIO)

Full metadata record

DC FieldValue Language
dc.contributor.authorSchlenk, Andreaen
dc.contributor.authorDiestel, Randien
dc.contributor.authorSasse, Florenzen
dc.contributor.authorSchobert, Raineren
dc.date.accessioned2017-02-17T15:22:55Z-
dc.date.available2017-02-17T15:22:55Z-
dc.date.issued2010-02-22-
dc.identifier.citationA selective 3-acylation of tetramic acids and the first synthesis of ravenic acid. 2010, 16 (8):2599-604 Chemistryen
dc.identifier.issn1521-3765-
dc.identifier.pmid20066698-
dc.identifier.doi10.1002/chem.200902544-
dc.identifier.urihttp://hdl.handle.net/10033/620829-
dc.description.abstract3-Acyltetramic acids, including delicate 3-oligoenoyl derivatives, such as the Penicillium metabolite ravenic acid, were prepared in two high-yielding steps. Reaction of tetramic acids with the ylide Ph(3)PCCO afforded exclusively the corresponding 3-acylylidenetetramic acids. These were amenable to Wittig olefinations with aliphatic, aromatic, saturated and unsaturated aldehydes after deprotonation with KOtBu. Due to its simplicity, selectivity and tolerance of pH-sensitive groups this method is superior to the established acylation protocols by Jones and Yoshii. It is also applicable to the synthesis of 3-acyltetronic acids. The new 3-oligoenoyl tetramic acids exhibited structure-dependent antimicrobial and cytotoxic activity.en
dc.language.isoenen
dc.rights.urihttp://creativecommons.org/licenses/by-nc-sa/4.0/*
dc.subject.meshAcylationen
dc.subject.meshAldehydesen
dc.subject.meshAlkenesen
dc.subject.meshAnti-Infective Agentsen
dc.subject.meshCatalysisen
dc.subject.meshPyrrolidinonesen
dc.subject.meshSpectrophotometry, Infrareden
dc.subject.meshStereoisomerismen
dc.titleA selective 3-acylation of tetramic acids and the first synthesis of ravenic acid.en
dc.typeArticleen
dc.contributor.departmentHelmholtz Centre for infection research, Inhoffenstr. 7, 38124 Braunschweig, Germany.en
dc.identifier.journalChemistry (Weinheim an der Bergstrasse, Germany)en

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