Total Synthesis of Flocoumafen via Knoevenagel Condensation and Intramolecular Ring Cyclization: General Access to Natural Products
The total synthesis and structure determination of cis- and trans-flocoumafen was described. The key synthetic steps involve Knoevenagel condensation with p-methoxybenzaldehyde, in situ decarboxylation and intramolecular ring cyclization to construct the tetralone skeleton. Stereospecific reduction...
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| Format: | Article |
| Language: | English |
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MDPI AG
2012-02-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/17/2/2091/ |
| _version_ | 1828496127559729152 |
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| author | Mankil Jung Oee-Sook Park Jeremy Ricci Dongguk Min Yongnam Lee Jae-Chul Jung Eunyoung Lim |
| author_facet | Mankil Jung Oee-Sook Park Jeremy Ricci Dongguk Min Yongnam Lee Jae-Chul Jung Eunyoung Lim |
| author_sort | Mankil Jung |
| collection | DOAJ |
| description | The total synthesis and structure determination of cis- and trans-flocoumafen was described. The key synthetic steps involve Knoevenagel condensation with p-methoxybenzaldehyde, in situ decarboxylation and intramolecular ring cyclization to construct the tetralone skeleton. Stereospecific reduction of the O-alkylated ketone 13 afforded good yield of precusor alcohol 5. Final coupling of alcohol 5 with 4-hydroxy-coumarin yielded flocoumafen (1). Separation and structure determination of cis- and trans-flocoumafen through 2D NMR analyses-assisted computer simulation techniques for the evaluation of anticoagulant activities are reported for the first time. This method is useful for generating the core tetralone skeleton of 4-hydroxycoumarin derivatives and provides a generalized access to various warfarin type anticoagulants. |
| first_indexed | 2024-12-11T12:24:24Z |
| format | Article |
| id | doaj.art-779a967a905c4b439425469b15202f37 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-11T12:24:24Z |
| publishDate | 2012-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-779a967a905c4b439425469b15202f372022-12-22T01:07:26ZengMDPI AGMolecules1420-30492012-02-011722091210210.3390/molecules17022091Total Synthesis of Flocoumafen via Knoevenagel Condensation and Intramolecular Ring Cyclization: General Access to Natural ProductsMankil JungOee-Sook ParkJeremy RicciDongguk MinYongnam LeeJae-Chul JungEunyoung LimThe total synthesis and structure determination of cis- and trans-flocoumafen was described. The key synthetic steps involve Knoevenagel condensation with p-methoxybenzaldehyde, in situ decarboxylation and intramolecular ring cyclization to construct the tetralone skeleton. Stereospecific reduction of the O-alkylated ketone 13 afforded good yield of precusor alcohol 5. Final coupling of alcohol 5 with 4-hydroxy-coumarin yielded flocoumafen (1). Separation and structure determination of cis- and trans-flocoumafen through 2D NMR analyses-assisted computer simulation techniques for the evaluation of anticoagulant activities are reported for the first time. This method is useful for generating the core tetralone skeleton of 4-hydroxycoumarin derivatives and provides a generalized access to various warfarin type anticoagulants.http://www.mdpi.com/1420-3049/17/2/2091/flocoumafenKnoevenagel condensationtetralone2D NMR analysiscomputer simulation |
| spellingShingle | Mankil Jung Oee-Sook Park Jeremy Ricci Dongguk Min Yongnam Lee Jae-Chul Jung Eunyoung Lim Total Synthesis of Flocoumafen via Knoevenagel Condensation and Intramolecular Ring Cyclization: General Access to Natural Products Molecules flocoumafen Knoevenagel condensation tetralone 2D NMR analysis computer simulation |
| title | Total Synthesis of Flocoumafen via Knoevenagel Condensation and Intramolecular Ring Cyclization: General Access to Natural Products |
| title_full | Total Synthesis of Flocoumafen via Knoevenagel Condensation and Intramolecular Ring Cyclization: General Access to Natural Products |
| title_fullStr | Total Synthesis of Flocoumafen via Knoevenagel Condensation and Intramolecular Ring Cyclization: General Access to Natural Products |
| title_full_unstemmed | Total Synthesis of Flocoumafen via Knoevenagel Condensation and Intramolecular Ring Cyclization: General Access to Natural Products |
| title_short | Total Synthesis of Flocoumafen via Knoevenagel Condensation and Intramolecular Ring Cyclization: General Access to Natural Products |
| title_sort | total synthesis of flocoumafen via knoevenagel condensation and intramolecular ring cyclization general access to natural products |
| topic | flocoumafen Knoevenagel condensation tetralone 2D NMR analysis computer simulation |
| url | http://www.mdpi.com/1420-3049/17/2/2091/ |
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