Total Synthesis of (±)-Isoperbergins and Correction of the Chemical Structure of Perbergin.

On the basis of its reported chemical structure, perbergin, a Rhodococcus fascians virulence quencher from the bark of Dalbergia pervillei, and its isomer were synthesized in nine steps with a 13.5% yield. However, the NMR spectra of the synthetic products were inconsistent with those reported in the literature. Re-evaluation of the 1D and 2D NMR spectra of the natural product perbergin revealed that the geranyl moiety of this compound is located at C-6 and has an E-configuration, instead of the reported C-8 geranylation with a Z-configuration. Interestingly, the synthetic isoperbergins demonstrated good antibacterial activity against R. fascians, Mycobacterium smegmatis, and Staphylococcus aureus, but not against the Gram-negative bacteria Pseudomonas aeruginosa and Escherichia coli.