Related Experiment Video
Updated: Jun 21, 2026
A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products
Published on: October 4, 2019
A new longipinene diester from Stevia monardifolia Kunth
Rodrigo E Rojas-Pérez1, Ernestina Cedillo-Portugal, Pedro Joseph-Nathan
1Departamento de Química Orgánica, Escuela Nacional de Ciencias Bioldgicas, Instituto Politécnico Nacional, Prolongación de Carpio y Plan de Ayala, Col. Santo Tomas, DF México, 11340 Mexico.
Abstract:
Nonpolar and medium polarity fractions from whole plant methanolic extracts of Stevia monardifolia afforded the new 7beta-angeloyloxy-8alpha-isovaleroyloxylongipin-2-en-1-one 1 along with known 7beta,8alpha-diangeloyloxylongipin-2-en-1-one 2 and 7beta,8alpha-diangeloyloxylongipinan-1-one 3. Alkaline hydrolysis of a mixture of 1 and 2 gave 7beta,8alpha-dihydroxylongipin-2-en-lone 4 which was subjected to a single crystal X-ray diffraction study. The new compound 1, which is the third 7beta,8alpha-dihydroxylongipin-2-en-1-one diester natural product isolated from a Stevia especies, was fully characterized by one- and two-dimensional NMR spectroscopy and its absolute configuration was confirmed as the 4R,5S,7S,8S,10R,11R enantiomer by vibrational circular dichroism (VCD) measurements in comparison to calculation at the B3LYP/DGDZVP level of theory.
Related Concept Videos
01:57Preparation of Diols and Pinacol Rearrangement
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
01:27Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview