A synthetic approach to the structure reported for the naturally isolated alkaloid named taifine has been developed. The structural assignment is established by spectral data: IR UV 1H-nmr and 13C-nmr. However, both the spectral and physical properties indicate that synthetic and natural taifine are different in constitution, suggesting the original structure assigned for taifine should be revised. Recently, a novel furo(2,3-b)quinolin-4-one named taifine was isolated from Ruta chalepensis L. (Rutaceae) by E1-Tawil and co-workers, and was assigned to be 9-ethyl-7-methoxy-4, 9-dihydrofuro(2,3-b)quinolin-4-one (1) purely based upon the spectral data2. As a part of our continuing interest in the synthesis and biological activities of furo(2,3-b)quinolin-4-one derivativens1, we carried out a synthetic approach to the structure reported for taifine using the modified Tuppy and Bohm's procedures3. We now report the results from this synthetic investigation which we believe should suggest that the proposed structure for taifine needs reinvestigation.
