These tools will no longer be maintained as of December 31, 2024. Archived website can be found here. PubMed4Hh GitHub repository can be found here. Contact NLM Customer Service if you have questions.


Pubmed for Handhelds

PUBMED FOR HANDHELDS

Search MEDLINE/PubMed

  • Title: Synthesis of the natural product building block 5-(3-bromophenyl)-4-hydroxy-5-methylhexan-2-one and its chiral characterization by using chiroptical spectroscopy.
    Author: De Gussem E, Cornelus J, Pieters S, Van den Bossche D, Van der Eycken J, Herrebout W, Bultinck P.
    Journal: Chemphyschem; 2013 Oct 07; 14(14):3255-62. PubMed ID: 23943592.
    Abstract:
    The absolute configuration of 5-(3-bromophenyl)-4-hydroxy-5-methylhexan-2-one, an intermediate in the synthesis of various natural products, is assigned by using vibrational circular dichroism (VCD), electronic circular dichroism (ECD), and optical rotatory dispersion (ORD). Experimental spectra were compared to density functional theory (DFT) calculations of the molecule with known configuration. These three techniques independently confirm that the absolute configuration is (S)-5-(3-bromophenyl)-4-hydroxy-5-methylhexan-2-one, thus enabling us to assign the absolute configuration with high reliability. The reliability of the VCD analysis was assessed quantitatively by using the CompareVOA program. We found that, in cases in which the agreement between theory and experiment was very good, a value of 10 cm(-1) for the triangular weighting function gave a more-realistic discriminative power between enantiomers than the default value of 20 cm(-1).
    [Abstract] [Full Text] [Related] [New Search]