The proposed structures of phenolic compounds isolated from Piper betle L. differ from those of the compounds obtained by total synthesis

We describe the syntheses of phenolic compounds, 4-[(1E, 3E, 5E)-6-(4-octyloxyphenyl)hexa-1,3,5-trien-1-yl]benzene-1,2-diol (1) and 3-(n-dodecyloxy) phenol (2), isolated from Piper betle. The triene moiety of 4-[(1E, 3E, 5E)-6-(4-octyloxyphenyl)hexa-1,3,5-trien-1-yl]benzene-1,2-diol was formed via two different methods, the Horner-Wadsworth-Emmons reaction and the McMurry coupling reaction. The spectral data of synthesized compounds show differences with those of reported as the naturally occurring compounds.

Automated summary

The syntheses of two phenolic compounds isolated from Piper betle, 4-[(1E, 3E, 5E)-6-(4-octyloxyphenyl)hexa-1,3,5-trien-1-yl]benzene-1,2-diol and 3-(n-dodecyloxy) phenol, were described. The triene moiety of 4-[(1E, 3E, 5E)-6-(4-octyloxyphenyl)hexa-1,3,5-trien-1-yl]benzene-1,2-diol was formed using two different methods, resulting in spectral data differences compared to naturally occurring compounds.