4.6 Article

VCD to determine absolute configuration of natural product molecules: secolignans from Peperomia blanda

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 10, Issue 21, Pages 4208-4214

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c2ob25109d

Keywords

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Funding

  1. State of Sao Paulo Research Foundation [FAPESP 2009/51850-9]
  2. FAPESP [2008/58658-3]
  3. CAPES
  4. Center for Scientific Computing (NCC/GridUNESP) of the Sao Paulo State University (UNESP)
  5. CNPq

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The absolute configuration and solution-state conformers of three peperomin-type secolignans isolated from Peperomia blanda (Piperaceae) are unambiguously determined by using vibrational circular dichroism (VCD) spectroscopy associated with density functional theory (DFT) calculations. Advantages of VCD over the electronic form of CD for the analysis of diastereomers are also discussed. This work extends our growing knowledge about secondary metabolites within the Piperaceae family species while providing a definitive and straightforward method to assess the absolute stereochemistry of secolignans.

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