Total Synthesis of Flocoumafen via Knoevenagel Condensation and Intramolecular Ring Cyclization General Access to Natural Products 英文参考文献.docVIP

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Total Synthesis of Flocoumafen via Knoevenagel Condensation and Intramolecular Ring Cyclization General Access to Natural Products 英文参考文献.doc

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Total Synthesis of Flocoumafen via Knoevenagel Condensation and Intramolecular Ring Cyclization General Access to Natural Products 英文参考文献

Molecules 2012, 17, 2091-2102; doi:10.3390/moleculeOPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Communication Total Synthesis of Flocoumafen via Knoevenagel Condensation and Intramolecular Ring Cyclization: General Access to Natural Products Jae-Chul Jung 1,?, Eunyoung Lim 2,?, Yongnam Lee 2, Dongguk Min 2, Jeremy Ricci 2, Oee-Sook Park 3,* and Mankil Jung 2,* 1 Department of Neuroscience and Medical Research Institute, School of Medicine, Ewha Womans University, Seoul 158-710, Korea 2 Department of Chemistry, Yonsei University, Seoul 120-749, Korea 3 Department of Chemistry, Institute for Basic Sciences, College of Natural Sciences, Chungbuk National University, Cheongju 361-763, Chungbuk, Korea ? These authors contributed equally to this work. * Authors to whom correspondence should be addressed; E-Mails: ospark@cbnu.ac.kr (O.-S.P.); mjung@yonsei.ac.kr (M.J.); Tel.: +82-43-261-2283 (O.-S.P.); Fax: +82-43-267-2279 (O.-S.P.); Tel.: +82-2-2123-2648 (M.J.); Fax: +82-2-364-7050 (M.J.). Received: 4 January 2012; in revised form: 9 February 2012 / Accepted: 14 February 2012 / Published: 21 February 2012 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-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 pr