Quantum-chemical calculations on the electronic circular dichroism of (-)-dibromophakellin and (-)-dibromophakell-statin.
The CD spectra of the pyrrole-imidazole alkaloids, (-)-dibromophakellin and (-)-dibromophakellstatin, have been calculated employing the quantum-chemical time-dependent density functional theory. Comparison of calculated and measured spectra showed that this well-established method is also a useful tool to elucidate the absolute stereochemistry of this class of compounds. The computational results have further been used to analyze the spectra measured in methanol and to explain the remarkable red shift of one CD band when trifluoroethanol is used as a solvent instead of methanol.
Atodiresei
Iuliana
I
Institute of Organic Chemistry, RWTH Aachen University, Aachen, Germany.
Zöllinger
Michael
M
Lindel
Thomas
T
Fleischhauer
Jörg
J
Raabe
Gerhard
G
D047230:Agelas / Q000737:chemistry; D000470:Alkaloids / Q000737:chemistry; D000818:Animals; D002942:Circular Dichroism; D004563:Electrochemistry; D007093:Imidazoles / Q000737:chemistry*; D015394:Molecular Structure; D010879:Piperazines / Q000737:chemistry*; D011789:Quantum Theory; D013237:Stereoisomerism
D000470:Alkaloids; D007093:Imidazoles; D010879:Piperazines; C104805:dibromophakellstatin; C465248:phakellin