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Total synthesis of flocoumafen via knoevenagel condensation and intramolecular ring cyclization: General access to natural products

Title
Total synthesis of flocoumafen via knoevenagel condensation and intramolecular ring cyclization: General access to natural products
Authors
Jung J.-C.Lim E.Lee Y.Min D.Ricci J.Park O.-S.Jung M.
Ewha Authors
정재철
Issue Date
2012
Journal Title
Molecules
ISSN
1420-3049JCR Link
Citation
vol. 17, no. 2, pp. 2091 - 2102
Indexed
SCIE; SCOPUS WOS scopus
Abstract
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-hydroxycoumarin 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.
DOI
10.3390/molecules17022091
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의학전문대학원 > 의학과 > Journal papers
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