Determination of the Absolute Configurations of Pharmacological Natural Products via Density Functional Theory Calculations of Vibrational Circular Dichroism: The New Cytotoxic Iridoid Prismatomerin
Citations Over TimeTop 11% of 2007 papers
Abstract
A new highly cytotoxic iridoid has very recently been isolated from Prismatomeris tetrandra and shown to have the structure 3, similar to that of the iridoid oruwacin, 2. We report the determination of the absolute configuration (AC) of the new iridoid, prismatomerin, using vibrational circular dichroism (VCD) spectroscopy. The VCD spectrum of the acetate derivative of 3, 4, is analyzed using the Stephens theory of VCD and density functional theory (DFT). The AC of the naturally occurring 3 is shown to be 1R,5S,8S,9S,10S, identical to that of the naturally occurring iridoid plumericin, 1, also determined using VCD spectroscopy. The [alpha]D values of the natural products 3 and 1 are negative and positive, respectively. Since the ACs of 3 and 1 are identical, it follows that the AC of 3 cannot be correctly determined by empirical comparison of the signs of the [alpha]D values of 3 and 1.
Related Papers
- → Absolute configuration determination of chiral molecules in the solution state using vibrational circular dichroism(2003)507 cited
- → Absolute configuration of diterpenoids from Jatropha dioica by vibrational circular dichroism(2016)14 cited
- → Determination of the Absolute Configuration of (−)-Mirtazapine by Vibrational Circular Dichroism(2002)26 cited
- → Vibrational Circular Dichroism for the Assignment of Absolute Configuration of Natural Products in Brazil(2021)6 cited
- → Absolute configuration assignment of (+)‐fluralaner using vibrational circular dichroism(2017)9 cited