Related Experiment Video
Updated: Jun 16, 2026

Enzymatic Synthesis of Epoxidized Metabolites of Docosahexaenoic, Eicosapentaenoic, and Arachidonic Acids
Published on: June 28, 2019
Total synthesis and absolute configuration of the marine norditerpenoid xestenone
Koichiro Ota1, Takao Kurokawa, Etsuko Kawashima
1School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo, Japan. otak@toyaku.ac.jp
Abstract:
Xestenone is a marine norditerpenoid found in the northeastern Pacific sponge Xestospongia vanilla. The relative configuration of C-3 and C-7 in xestenone was determined by NOESY spectral analysis. However the relative configuration of C-12 and the absolute configuration of this compound were not determined. The authors have now achieved the total synthesis of xestenone using their developed one-pot synthesis of cyclopentane derivatives employing allyl phenyl sulfone and an epoxy iodide as a key step. The relative and absolute configurations of xestenone were thus successfully determined by this synthesis.
Related Concept Videos
Stereoisomerism of Cyclic Compounds
Aromatic Hydrocarbon Cations: Structural Overview
Removing one hydrogen from the intervening CH2 group with both...
¹³C NMR: Distortionless Enhancement by Polarization Transfer (DEPT)
¹H NMR: Complex Splitting
Splitting diagrams or splitting tree diagrams are routinely used to depict such complex couplings. While drawing splitting diagrams, the splitting with the larger coupling constant is usually applied first.
Esters to β-Ketoesters: Claisen Condensation Overview
Esters to β-Ketoesters: Claisen Condensation Mechanism

