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


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 provides a generalized access to various warfarin type anticoagulants.

SUBMITTER: Jung JC 

PROVIDER: S-EPMC6268178 | biostudies-literature | 2012 Feb

REPOSITORIES: biostudies-literature

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

Jung Jae-Chul JC   Lim Eunyoung E   Lee Yongnam Y   Min Dongguk D   Ricci Jeremy J   Park Oe-Sook OS   Jung Mankil M  

Molecules (Basel, Switzerland) 20120221 2


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  ...[more]

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