The constituents of the resin of Euryops floribundus. N.E.Br.

Abstract

The aerial portions of the plant Euryops floribundus were extracted and shown to contain Euryopsonol and another sesquiterpenoid for which the name Euryopsol is proposed. An extraction of Euryops tenuissimus contained Euryopsol only. Euryopsonol, of empirical formula C₠₅ H₂₀ O₃, was previously shown to contain a hydroxyl group and a keto-group and to be doubly unsaturated. The hydroxyl group has been shown to be secondary, while the keto-group is ⋉, β, γ, δ-unsaturated, Spectroscopic and Mass spectrosmetric measurements showed euryopsonol to possess a furan ring and to be member of the eremophilane -9 of sesquiterpenoids . These proposals were confirmed by the conversion of euryopsonol to furanoeremophilone -9, thus establishing the stereochemistry at C₄, C₅ and C₠₀. This free hydroxyl group has been placed at C₃, but its stereochemistry is still unknown. Euryopsol, of empirical formula C₠₅ H₂₂ O₄, possesses an unstable furan ring and readily undergoes autoxidation, probably to a more stable ¥-lactone. It contains two vicinal hydroxyl groups, one of which was placed by Mass spectrometry at C₉. If euryopsol possesses the eremophilane skeleton the other hydroxyl group must be at C₠₀.