doi: 10.1016/j.tetlet.201711008.
Epub 2017 Nov 7.
Absolute Configurations of Griseorhodins A and C
Affiliations
- PMID: 29503481
- PMCID: PMC5828249
- DOI: 10.1016/j.tetlet.201711008
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Absolute Configurations of Griseorhodins A and C
Humberto E Ortega et al.
Tetrahedron Lett.
.
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Abstract
The known antibiotic and cytotoxic compounds griseorhodin A (1) and griseorhodin C (2) were produced in solid culture by Streptomyces puniceus AB10, which was isolated from the leaf-cutter ant Acromyrmex rugosus rugosus. Their absolute configurations were unambiguously established as 6S,6aR,7S,8S and 6R,6aR,7S,8R, respectively, using vibrational circular dichroism (VCD) and density functional theory (DFT) calculations.
Keywords: Acromyrmex rugosus rugosus; Griseorhodins; Rubromycin; Streptomyces puniceus; Vibrational circular dichroism.
Figures
Key NOE correlations of griseorhodin A (1) and C (2)
(Left) Comparison of the observed IR and VCD spectra of (−)-2 with the calculated (B3LYP/PCM(DMSO)/6-31G(d)) IR and VCD spectra of the lowest-energy conformer identified for (6R,6aR,7S,8R)-griseorhodin C (right). Numbers on spectra represent selected vibrational modes.
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