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Total structural assignment and absolute configuration of terreinol by 13C and 1H NMR

✍ Scribed by Fernando César de Macedo Jr; Anita Jocelyne Marsaioli

Publisher
John Wiley and Sons
Year
2005
Tongue
English
Weight
128 KB
Volume
43
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

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 Δδ^SR^ sign distribution, allowing reliable assignment of the R configuration for terreinol. Copyright © 2004 John Wiley & Sons, Ltd.

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