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

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.

Keywords::

• isochromen-1-one
• Geotrichum sp
• 3,5-dimethoxy-4-butylhomophthalic acid
• antibacterial

Acknowledgment

The authors are grateful to the Pakistan Science Foundation (PSF) for a research grant under Project No. PSF/Res/C-QU/CHEM (395).