Reactions of primulagenin A. II. Acid-catalysed transformation

Abstract

Treatment of primulagenin A with methanolic hydrochloric acid gave a complex mixture of products from which the known aegiceradiol (oleana- 12,15-diene-3β,28-dial) and aegiceradienol (28-noroleana-12,17(18)- dien-3β-ol) were obtained. In addition, three new products, a double- bond isomer of aegiceradiol, the structure of which has been established by synthesis, a C₃₀ aromatic alcohol, and a hydroxy ketone containing a cyclopropane ring, have been isolated.