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  • Total synthesis and antibacterial screening of ( ± )-7-butyl-6,8-dihydroxy-3-pentyl-3,4-dihydroisochromen-1-one.

Total synthesis and antibacterial screening of ( ± )-7-butyl-6,8-dihydroxy-3-pentyl-3,4-dihydroisochromen-1-one.

Journal of Asian natural products research (2013-07-23)
Aamer Saeed, Hummera Rafique, Muhammad Arshad
ABSTRACT

A new total synthesis of ( ± )-7-butyl-6,8-dihydroxy-3-pentyl-3,4-dihydroisochromen-1-one, isolated as R-enantiomer from Geotrichum sp., has been described. Reaction of 4-butyl-3,5-dimethoxyhomophthalic anhydride with hexanoyl chloride in the presence of 1,1,3,3-tetramethyl guanidine and triethyl amine afforded 7-butyl-6,8-dimethoxy-3-pentylisochromen-1-one, which was converted into corresponding 3,4-dihydroisochromen-1-one by successive ring opening and reduction. Final demethylation to furnish the natural product was achieved using anhydrous aluminum chloride in ethanethiol. The target compound and the intermediates were subjected to antibacterial evaluation against 10 bacterial strains using levofloxacin as standard.

MATERIALS
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Sigma-Aldrich
Hexanoyl chloride, purum, ≥98.0% (GC)
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Sigma-Aldrich
Hexanoyl chloride, ≥99%
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Sigma-Aldrich
Hexanoyl chloride, 97%
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