A selective 3-acylation of tetramic acids and the first synthesis of ravenic acid.
dc.contributor.author | Schlenk, Andrea | |
dc.contributor.author | Diestel, Randi | |
dc.contributor.author | Sasse, Florenz | |
dc.contributor.author | Schobert, Rainer | |
dc.date.accessioned | 2017-02-17T15:22:55Z | |
dc.date.available | 2017-02-17T15:22:55Z | |
dc.date.issued | 2010-02-22 | |
dc.identifier.citation | A selective 3-acylation of tetramic acids and the first synthesis of ravenic acid. 2010, 16 (8):2599-604 Chemistry | en |
dc.identifier.issn | 1521-3765 | |
dc.identifier.pmid | 20066698 | |
dc.identifier.doi | 10.1002/chem.200902544 | |
dc.identifier.uri | http://hdl.handle.net/10033/620829 | |
dc.description.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. | |
dc.language.iso | en | en |
dc.rights.uri | http://creativecommons.org/licenses/by-nc-sa/4.0/ | * |
dc.subject.mesh | Acylation | en |
dc.subject.mesh | Aldehydes | en |
dc.subject.mesh | Alkenes | en |
dc.subject.mesh | Anti-Infective Agents | en |
dc.subject.mesh | Catalysis | en |
dc.subject.mesh | Pyrrolidinones | en |
dc.subject.mesh | Spectrophotometry, Infrared | en |
dc.subject.mesh | Stereoisomerism | en |
dc.title | A selective 3-acylation of tetramic acids and the first synthesis of ravenic acid. | en |
dc.type | Article | en |
dc.contributor.department | Helmholtz Centre for infection research, Inhoffenstr. 7, 38124 Braunschweig, Germany. | en |
dc.identifier.journal | Chemistry (Weinheim an der Bergstrasse, Germany) | en |
refterms.dateFOA | 2018-06-13T07:23:40Z | |
html.description.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. |