Total structural assignment and absolute configuration of terreinol by 13C and 1H NMR.
The carbon-carbon connectivity of terreinol, a new metabolite isolated from Aspergillus terreus, and its previous (13)C assignments were confirmed by a two-dimensional INADEQUATE experiment using a few milligrams of the compound with natural (13)C abundance. The carbon-carbon correlations were determined by computational analysis (with >99% probability) of this experiment. Additionally, the absolute configuration of terreinol was achieved indirectly via its corresponding secondary alcohol by the modified Mosher method allied to conformational analysis. The shielding effect of the phenyl group of methoxytrifluoromethylphenylacetic acid (MTPA) on the substituents of the carbonylic centre gave a fully regular Deltadelta(SR) sign distribution, allowing reliable assignment of the R configuration for terreinol.
de Macedo
Fernando César
FC
Chemistry Institute, State University of Campinas, Brazil.
Marsaioli
Anita Jocelyne
AJ
D000465:Algorithms; D001230:Aspergillus / Q000737:chemistry*; D002247:Carbon Isotopes; D003461:Crystallography / Q000379:methods*; D005663:Furans / Q000032:analysis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods*; D008968:Molecular Conformation; D011522:Protons; D013141:Spiro Compounds / Q000032:analysis* / Q000737:chemistry*
D002247:Carbon Isotopes; D005663:Furans; D011522:Protons; D013141:Spiro Compounds; C500271:terreinol