Structure and absolute configuration of hydroxy-bis-dihydrofarinosin from Encelia farinosa

The structure of the dimeric eudesmanolide hydroxy-bis-dihydrofarinosin (1) from Encelia farinosa followed after contrasting their ¹H and ¹³C NMR spectra with those of encelin (6), hydroxy-bis-dihydroencelin (3), and farinosin (4). Structure 1 was verified by single-crystal X-ray diffraction analysis, which further provided the stereochemistry of the hydroxy group at C-4. Comparison of the experimental vibrational circular dichroism spectrum of its derived diacetate 2 with that calculated by density functional theory provided the absolute configuration, which resulted the same as that of its biogenetic precursor 4. Evaluation of several chemical shift differences between the two eudesmanolide fragments of 1 and 3 allows also ascertaining the yet not reported absolute configuration of the C-4 stereogenic center of 3.