Abstract
Abstract In order to examine the structure, “glut-5(10)-en-1-one”, proposed for a new triterpene from Euphorbia nerifolia, this ketone (≡ D : B-friedoolean-5(10)en-1-one) was prepared. Oxidation of D : B-friedoolean-5(10)-ene with chromium trioxide-pyridine complex gave the allylic oxidation products, D : B-friedoolean-5(10)-en-1-one, D : B-friedoolean-5(10)-en-6-one, and D : B-friedoolean-5(10)-ene-1,6-dione. The spectral data and physical constants of the synthetic ketone (D : B-friedoolean-5(10)-en-1-one) were not identical with those of the new triterpene; this requires revision of the structure of this natural triterpene. Oxidation of D : B-friedoolean-5(10)-en-3-one enol acetate under the same conditions to give D : B-friedooleane-1,5(10)-dien-3-one is also described.
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