22339-27-1Relevant articles and documents
STABLE CARBOCATIONS FROM TERPENOIDS. I. GENERATION OF CARBOCATIONS FROM NATURAL SESQUITERPENES - DERIVATIVES OF HEXAHYDRONAPHTHALENE
Osadchii, S. A.,Polovinka, M. P.,Korchagina, D. V.,Pankrushina, N. A.,Dubovenko, Zh. V.,et al.
, p. 1070 - 1081 (2007/10/02)
Stable enantio- and diastereomeric carbocations were generated for the first time from optically active sesquiterpenes (-)-α- and (-)-γ-murolenes (I) and (II) and (+)-γ- and (+)-δ-cadinenes (III) and (IV), and their rearrangements in media with various acidities were studied at tempetatures between -120 and 20 deg C.By the reaction of solutions of salts of the stable cations with nucleophiles the transition was realized from unconjugated dienes (I-IV), isolated from the resin of Pinus silvestris L., to the conjugated dienes (-)-zonarene (V), (-)- and (+)-10-epizonarenes (VI, VII), (-)-trans-isocadinene (VIII), and (-)-bicyclosesquiphellandrene (IX), which had been discovered previously in other plant sources.