Abstract
The esters ferovinal (α-apiene-type) and ferocin (γ-apiene-type) were isolated from Ferula ovina. Their structures were established by analyzing IR, PMR, and 13C NMR spectra; DEPT, HSQC, COSY, NOESY, and HMBC experiments; and X-ray crystal structure analyses (XSAs). The XSAs determined the molecular structures and absolute configurations of ferovinal and ferocin and established that their 11-membered humulane macrocycles adopted the 14,15U78 and 14,15U78 conformations. The C8 p-hydroxybenzoate groups in these apienes occupied β-equatorial positions. The only chiral center in ferovinal and ferocin had the 8S-configuration.
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