Documentation scienceplus.abes.fr version Bêta
AttributsValeurs
type
Is Part Of
Subject
Title
  • Determination of the Absolute Configurations of PharmacologicalNatural Products via Density Functional Theory Calculations ofVibrational Circular Dichroism: The New Cytotoxic IridoidPrismatomerin
has manifestation of work
related by
Author
Abstract
  • A new highly cytotoxic iridoid has very recently been isolated from Prismatomeris tetrandra and shownto have the structure 3, similar to that of the iridoid oruwacin, 2. We report the determination of theabsolute 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 theoryof VCD and density functional theory (DFT). The AC of the naturally occurring 3 is shown to be1R,5S,8S,9S,10S, identical to that of the naturally occurring iridoid plumericin, 1, also determined usingVCD spectroscopy. The [α]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 byempirical comparison of the signs of the [α]D values of 3 and 1.
article type
is part of this journal



Alternative Linked Data Documents: ODE     Content Formats:       RDF       ODATA       Microdata