Abstract

Several new N-acyl derivatives of 1-(4-hydroxy-2,3-dihydrobenzofuran-5-yl)-7,8-di methoxy-1,9 b,2,3,3 a,4-hexahydro-[1]benzopyrano[3,4-c]pyrazole-1-ene have been prepared by appropriate chemical transformation of isohydrazones of rotenone and amorphigenin. A study of their1H- and13C-NMR spectra confirmed the presence of the twocis 3aβ, 9bβ, 2′β and 3aα, 9bα, 2′β diastereomers in the parent isohydrazones and revealed the strong predominance of the conformers withendo orientation of the 3-NAc group. The conformations due to rotation about the 1,5′-bond between rings C and D in the 4′-OH and 4′-O-substituted compounds were also determined by taking into account the anisotropic effect of aromatic rings A and D, and the hydrogen bond between 4′-OH and the 2-N atom, as well as by inspecting the Dreiding models.

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