Assignment of Absolute Configuration of Known Anthraquinones

Among the new papers published by my group this year, we reported the assignment of the absolute configuration of the known fungal anthraquinones versicolorin C and versiconol. Both compounds have been first isolated several years ago. Versicolorin C was first isolated by Hamasaki and collaborators in 1967 (Agr. Biol. Chem. 1967, 31, 11) and versiconol has been first reported by the same group in 1969 (Hatsuda et al., Agric. Biol. Chem. Japan 1969, 33, 131). While there has been numerous investigations with these two compounds, their absolute configurations have never been reported.

We performed a complete spectroscopic analysis of both versicolorin C and versiconol. Moreover, the absolute configuration of both compounds have been established in collaboration with the group of Professor João Marcos Batista Jr. (Universidade Federal de São Paulo). We observed that, in the case of versiconol, the results of ECD analysis were solvent-dependent, an issue that demonstrates that such analyses should be performed with care in order to avoid stereochemical misassignments.

The complete manuscript can be assessed here.