Portal de Periódicos da CAPES

Stereostructure Reassignment and Absolute Configuration of Isoepitaondiol, a Meroditerpenoid from Stypopodium flabelliforme

2009; American Chemical Society; Volume: 73; Issue: 1 Linguagem: Inglês

10.1021/np900553p

1520-6025

Carlos Areche, Aurelio San-Martı́n, Juana Rovirosa, Marcelo A. Muñoz, A. Hernandez-Barragan, Marı́a A. Bucio, Pedro Joseph‐Nathan,

Phytochemistry and Biological Activities

Careful examination of the published NMR data for isoepitaondiol, a meroditerpenoid from Stypopodium flabelliforme, suggests that its published structure 1 must be revised. On the basis of extensive 1D and 2D NMR studies, we now propose that structure 2, with a trans-anti-trans-anti-cis arrangement fits isoepitaondiol diacetate. The relative configuration of 2 was confirmed by single-crystal X-ray diffraction, while the absolute configuration was evidenced by vibrational circular dichroism in combination with DFT B3LYP/DGDZVP calculations.