Egr. Fernandes et al., Synthesis and structural elucidation of xanthonolignoids: trans-(+/-)-kielcorin B and trans-(+/-)-isokielcorin B, HETEROCYCLE, 51(4), 1999, pp. 821-828
This paper reports the synthesis and characterization of two isomeric xanth
onolignoids - trans-(+/-)-kielcorin B and trans-(+)-isokielcorin B. The syn
thetic approach is based on the oxidative coupling of 2,3-dihydroxy-4-metho
xyxanthone with coniferyl alcohol in the presence of silver carbonate. The
structural elucidation of these compounds was achieved by extensive NMR stu
dies:H-1 and C-13 NMR spectra, homonuclear correlation spectroscopy (COSY,
COSYLR), heteronuclear correlation spectroscopy (HETCOR), nuclear Overhause
r effect (NOE) and one-dimensional selective INEPT. The NMR spectroscopic t
echniques used in this study led to an unambiguous characterisation of tran
s-(+/-)-kielcorin B and trans-(+/-)-isokielcorin B, which includes the assi
gnment of all proton and carbon resonances and the establishment of the sub
stituents orientation and protons configurational relationship on their 1,4
-dioxane ring.