Terpenoids and related compounds. Part 24. Molecular rearrangements in friedo-oleanenes

Abstract

D:A-Friedo-oleana-3,7-diene (10) underwent rearrangement on refluxing with hydrochloric acid in acetic acid to give the conjugated diene (12)[oleana-11,13(18)-diene]. Further, the action of phosphoryl chloride and pyridine on the 7-hydroxy-3-acetates (13) and (19) furnished the 7-ene-3-acetates (14) and (20), respectively. On the other hand the action of perchloric acid in acetic anhydride on (13) and (19) furnished the rearranged 14-ene-3-acetates (15) and (21), respectively. A part of this work constituted a correction of previously published work.