VCD determination of the absolute configuration of stypotriol.
The absolute configuration of the pentacyclic ichthyotoxin stypotriol, a constituent of Stypopodium zonale, was deduced to be 3S,5R,8R,9R,10S,13S,14S-(-)-1 by vibrational circular dichroism spectroscopy of the derived triacetate 2 in comparison to DFT B3LYP/DGDZVP calculations. Compound 2, C33H46O7 having 300 electrons, is the largest natural product successfully studied by VCD to date.
Muñoz
Marcelo A
MA
Instituto de Química, Facultad de Ciencias, Universidad Austral de Chile, Casilla 567, Valdivia, Chile.
Areche
Carlos
C
San-Martín
Aurelio
A
Rovirosa
Juana
J
Joseph-Nathan
Pedro
P
D002942:Circular Dichroism; D008958:Models, Molecular; D008968:Molecular Conformation; D010140:Pacific Ocean; D000459:Phaeophyceae / Q000737:chemistry*; D011114:Polynesia; D013729:Terpenes / Q000737:chemistry* / Q000302:isolation & purification; D014732:Vibration
D013729:Terpenes; C094447:stypotriol